Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 1995793Notes

Reaction equation

HRID 1995793 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH:19][CH:20]=[O:21])[S:17][CH:18]=1)[C:11]([OH:13])=O)[CH3:7].[CH3:22][N+:23]([CH3:26])=[CH:24][Cl:25].[Cl-].C[Si](CC(N)=O)(C)C.[NH2:36][CH:37]1[C:57](=[O:58])[N:39]2[C:40]([C:54]([OH:56])=[O:55])=[C:41]([CH2:44][S:45][C:46]3[N:50]([CH2:51][C:52]#[CH:53])[N:49]=[N:48][N:47]=3)[CH2:42][S:43][C@H:38]12.C(=O)(O)[O-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[CH3:22][N+:23]([CH3:26])=[CH:24][Cl:25].[Cl-:3].[CH2:6]([O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH:19][CH:20]=[O:21])[S:17][CH:18]=1)[C:11]([NH:36][CH:37]1[C:57](=[O:58])[N:39]2[C:40]([C:54]([OH:56])=[O:55])=[C:41]([CH2:44][S:45][C:46]3[N:50]([CH2:51][C:52]#[CH:53])[N:49]=[N:48][N:47]=3)[CH2:42][S:43][C@H:38]12)=[O:13])[CH3:7]

Participants

13

Reactant 7

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 516892Sodium BicarbonateHCID 130511567-amino-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidHCID 544580772-(2-Formamidothiazol-4-yl)-2-ethoxyiminoacetic acid

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 1317130877-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Vilsmeier reagent was prepared from N,N-dimethylformamide (0.4 g) and phosphoryl chloride (0.8 g) in a conventional manner. 2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.1 g) was added to the stirred suspension of Vilsmeier reagent in dry tetrahydrofuran (15 ml) under ice cooling and stirred for 30 minutes at same temperature [Solution A]. Trimethylsilylacetamide (4.5 g) was added to the stirred suspension of 7-amino-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (1.5 g) in dry ethyl acetate (30 ml). To the solution obtained was dropwise added the Solution A at -10° C. and the resulting solution was stirred at same temperature for 0.5 hours. Water (40 ml) was added to the resulting solution, and the separated organic layer was added to water, and the mixture was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated to give 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.72 g).

Workup

  1. customTo the solution obtained
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-e82cfe4ece7346e09e30c7f90ab66a91
Source dataset
uspto-grants-1983_09
Patent number
US04405617

Reaction notes

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