Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 371244Notes

Reaction equation

HRID 371244 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([OH:16])=O)[CH2:10][CH2:9][CH:8]=[CH:7]1.[ClH:25].C1(ON)CCCC=C1.[NH2:34][CH:35]1[C:56](=[O:57])[N:37]2[C:38]([C:53]([OH:55])=[O:54])=[C:39]([CH2:42][S:43][C:44]3[CH:45]=[CH:46][C:47]4[N:48]([N:50]=[N:51][N:52]=4)[N:49]=3)[CH2:40][S:41][C@H:36]12.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C.CC(C)=O.CN(C)C=O>[CH3:36][N+:37]([CH3:56])=[CH:38][Cl:25].[Cl-:3].[CH:6]1([O:11][N:12]=[C:13]([C:17]2[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=2)[C:14]([NH:34][CH:35]2[C:56](=[O:57])[N:37]3[C:38]([C:53]([OH:55])=[O:54])=[C:39]([CH2:42][S:43][C:44]4[CH:45]=[CH:46][C:47]5[N:48]([N:50]=[N:51][N:52]=5)[N:49]=4)[CH2:40][S:41][C@H:36]23)=[O:16])[CH2:10][CH2:9][CH:8]=[CH:7]1

Participants

14

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 13345661HCID 13345661, compoundHCID 20274566(2-Cyclohexen-1-yl)oxyamine hydrochloride2×HCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317130267-[2-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 6

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-3 °C

Procedure

The solution of Vilsmeier reagent was prepared from dry N,N-dimethylformamide (0.4 g), phosphoryl chloride (0.8 g) and dry ethyl acetate (1.6 ml) in a usual manner. To the solution were added dry tetrahydrofuran (18 ml) and 2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.2 g) and then stirred at -3° to 3° C. (Solution A). A mixture of 7-amino-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (1.5 g), sodium carbonate (0.9 g) and water (9.0 ml) was stirred to give a homogeneous solution. After the addition of acetone (9.0 ml), the solution was cooled to -3° C. and then thereto was added Solution A over a period of 5 minutes, keeping the temperature at -3° to 3° C. and the pH at 7.5 to 8.5 with triethyl amine. The resulting mixture was stirred for 30 minutes at the same temperature and pH. To the reaction mixture were added water, ethyl acetate and tetrahydrofuran. The resulting mixture was adjusted to pH 2.0 with 10% hydrochloric acid and filtered. The organic layer was separated from the filtrate, washed with water (×3), dried over magnesium sulfate, treated with activated charcoal and then evaporated. The residue was pulverized in isopropyl ether. The powder was collected by filtration, washed with isopropyl ether and then dried to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.83 g).

Workup

  1. customto give a homogeneous solution
  2. customat -3° to 3° C.
  3. stirringThe resulting mixture was stirred for 30 minutes at the same temperature and pH
  4. filtrationfiltered
  5. customThe organic layer was separated from the filtrate
  6. washwashed with water (×3)
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with activated charcoal
  9. customevaporated
  10. filtrationThe powder was collected by filtration
  11. washwashed with isopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-2908df67ad784392849b72d775e8b2ba
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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