Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 615415Notes

Reaction equation

HRID 615415 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:21]=[CH:22][S:23][CH:24]=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+].[Na+].Cl>C(OCC)(=O)C.C(=O)(O)[O-].[Na+].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:21]=[CH:22][S:23][CH:24]=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 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 13345661HCID 13345661, compoundHCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 131714109HCID 131714109, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

Vilsmeier reagent was prepared from phosphorus oxychloride (1.6 g) and N,N-dimethylformamide (0.8 g) in ethyl acetate (3.2 ml) in a usual manner. 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (2.5 g) was added to the stirred suspension of Vilsmeier reagent in ethyl acetate (20 ml) under ice-cooling and the resultant mixture was stirred for 20 minutes at the same temperature to produce an activated acid solution. 7-Amino-3-(tetrazolo[1,5-b]-pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (3.5 g) was dissolved in a solution of sodium bicarbonate (2.4 g) in a mixture of water (26 ml) and acetone (26 ml). To the solution was added the activated acid solution obtained above at -3° to 3° C. and the solution was stirred for 30 minutes under keeping the pH 7 to 8 with 20% aqueous solution of sodium carbonate. Water and ethyl acetate 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-(4-thiazolyl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (3.7 g).

Workup

  1. temperaturecooling
  2. customto produce an activated acid solution
  3. additionTo the solution was added the activated acid solution
  4. customobtained above at -3° to 3° C.
  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-42010ffc44ac4d3594a5b029d9efa667
Source dataset
uspto-grants-1985_02
Patent number
US04499088

Reaction notes

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