Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1463071Notes

Reaction equation

HRID 1463071 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]([O:10][C:11]([CH2:13][O:14][N:15]=[C:16]([C:20]1[N:24]=[CH:23][S:22][N:21]=1)[C:17]([OH:19])=O)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:28].[Cl-].[NH2:31][CH:32]1[C:53](=[O:54])[N:34]2[C:35]([C:50]([OH:52])=[O:51])=[C:36]([CH2:39][S:40][C:41]3[CH:42]=[CH:43][C:44]4[N:45]([N:47]=[N:48][N:49]=4)[N:46]=3)[CH2:37][S:38][C@H:33]12.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)(=O)C.O.CC(C)=O.CN(C)C=O>[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:28].[Cl-:3].[C:6]([O:10][C:11]([CH2:13][O:14][N:15]=[C:16]([C:20]1[N:24]=[CH:23][S:22][N:21]=1)[C:17]([NH:31][CH:32]1[C:53](=[O:54])[N:34]2[C:35]([C:50]([OH:52])=[O:51])=[C:36]([CH2:39][S:40][C:41]3[CH:42]=[CH:43][C:44]4[N:45]([N:47]=[N:48][N:49]=4)[N:46]=3)[CH2:37][S:38][C@H:33]12)=[O:19])=[O:12])([CH3:7])([CH3:8])[CH3:9]

Participants

13

Reactant 7

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 516892Sodium BicarbonateHCID 13345661HCID 13345661, compoundHCID 539872492-Tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317136127-[2-t-Butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

Vilsmeier reagent was prepared from phosphorus oxychloride (1.4 g) and N,N-dimethylformamide (0.65 g) in ethyl acetate (2.6 ml) in a usual manner. 2-t-Butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (2.1 g) was added to the stirred suspension of Vilsmeier reagent in ethyl acetate (20 ml) under ice-cooling and the mixture was stirred for 30 minutes at the same temperature to prepare an activated acid solution. 7-Amino-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (3.0 g) was dissolved to the solution of sodium bicarbonate (2.1 g) in water (25 ml) and acetone (25 ml). To the solution was added the above activated acid solution at -3° to 3° C. and the solution was stirred for 30 minutes under keeping the pH 7 to 8 with 20% an aqueous solution of sodium carbonate. Ethyl acetate and water were added to the reaction mixture and the mixture was adjusted to pH 2.0 with 10% hydrochloric acid. The separated organic layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-t-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3 -yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4.07 g).

Workup

  1. temperaturecooling
  2. customto prepare an activated acid solution
  3. additionTo the solution was added the above activated acid solution at -3° to 3° C.
  4. stirringthe solution was stirred for 30 minutes
  5. washThe separated organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8c6b11bc267543108f19214b61b2b24a
Source dataset
uspto-grants-1984_07
Patent number
US04463003

Reaction notes

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