Hydrochloric Acid → Chloro-N,N-dimethylformiminium chloride

HRID 2412749Notes

Reaction equation

HRID 2412749 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][S:7][CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[C:17]([NH:20][CH:21]=[O:22])[S:18][CH:19]=1)[C:12]([OH:14])=O.[NH2:23][CH:24]1[C:44](=[O:45])[N:26]2[C:27]([C:41]([OH:43])=[O:42])=[C:28]([CH2:31][S:32][C:33]3[N:37]([CH2:38][CH:39]=[CH2:40])[N:36]=[N:35][N:34]=3)[CH2:29][S:30][C@H:25]12.[ClH:46]>O.CC(C)=O.C(OCC)(=O)C.C(N(CC)CC)C.O1CCCC1.CN(C)C=O>[CH3:25][N+:26]([CH3:44])=[CH:27][Cl:46].[Cl-:3].[CH3:6][S:7][CH2:8][O:9][N:10]=[C:11]([C:15]1[N:16]=[C:17]([NH:20][CH:21]=[O:22])[S:18][CH:19]=1)[C:12]([NH:23][CH:24]1[C:44](=[O:45])[N:26]2[C:27]([C:41]([OH:43])=[O:42])=[C:28]([CH2:31][S:32][C:33]3[N:37]([CH2:38][CH:39]=[CH2:40])[N:36]=[N:35][N:34]=3)[CH2:29][S:30][C@H:25]12)=[O:14]

Participants

12

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 53744847HCID 53744847, compoundHCID 704326537-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 131712582HCID 131712582, compound

Reagents, catalysts & solvents 6

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

The Vilsmeier reagent was prepared from dry dimethylformamide (0.209 g), phosphorus oxychloride (0.434 g) and dry ethyl acetate (0.75 ml) by the conventional method. Dry tetrahydrofuran (6.5 ml) was added thereto and then 2-methylthiomethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer)(0.65 g) was added thereto at 0° C. The mixture was stirred for 30 minutes at the same temperature. The resulting mixture was dropwise added at -5° to 0° C. to a stirred solution of 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.25 g) in a mixture of water (10 ml) and acetone (10 ml) keeping the pH at 7.5 by triethylamine, and the mixture was stirred for 30 minutes at the same temperature at pH 7.5. To the reaction mixture was added ethyl acetate (60 ml) and the mixture was adjusted to pH 2.5 with 10% hydrochloric acid. Insoluble material was filtered off and the filtrate was extracted twice with ethyl acetate. The combined extracts were washed twice with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off and the residue was pulverized with diethyl ether to give yellowish powder of 7-[2-methylthiomethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer)(1.03 g).

Workup

  1. customat 0° C
  2. stirringthe mixture was stirred for 30 minutes at the same temperature at pH 7.5
  3. filtrationInsoluble material was filtered off
  4. extractionthe filtrate was extracted twice with ethyl acetate
  5. washThe combined extracts were washed twice with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-fd6c1e8e243b4514bbd67340b8b0eb13
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

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