Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1074941노트

반응식

HRID 1074941 반응식
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

참가 물질

14

반응물 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 13345661HCID 13345661, 화합물HCID 20274566(2-Cyclohexen-1-yl)oxyamine hydrochloride2회HCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acid

생성물 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

시약·촉매·용매 6

HCID 180Acetone용매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매2회

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온도
-3 °C

실험 절차

The solution of Vilsmeier reagent was prepared from dry N,N-dimethylformamide (0.4 g), phosphoryl chloride (0.8 ) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-0275ec594ee9443a818b08993d6467c5
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04394384

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