Hydrochloric Acid → 2,2,2-Trichloroethyl 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylate

HRID 1764009Notes

Reaction equation

HRID 1764009 reaction equation
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH2:19])[C@H:5]2[S:4]1.C(N(CC)CC)C.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>ClCCl.CN(C)C1C=CC=CC=1>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:14])[Cl:15])=[O:10])[N:6]2[C:17](=[O:20])[CH:18]([NH:19][C:35]([NH:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:36])[C@H:5]2[S:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 128341352,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 128340092,2,2-Trichloroethyl 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylateYield 90.4%

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineCatalystHCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (3.82 g) was suspended in dichloromethane (30 ml), and then dissolved by adding triethylamine (0.9 g) and dimethylaniline (0.1 g). To the solution was added phenylisocyanate (1.2 g) under stirring and ice-cooling, and the mixture was stirred for 5 hours. 10% Hydrochloric acid was added to the reaction mixture, and the mixture was stirred for 10 minute. The reaction mixture was filtered, and the dichloromethane layer was separated from the filtrate, washed in turn with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off to give 2,2,2-trichloroethyl 2-methyl-7-(3-phenylureido)-3-cephem-4-carboxylate (4.2 g), mp 172° to 174° C.

Workup

  1. dissolutiondissolved
  2. temperatureice-cooling
  3. stirringthe mixture was stirred for 5 hours
  4. stirringthe mixture was stirred for 10 minute
  5. filtrationThe reaction mixture was filtered
  6. customthe dichloromethane layer was separated from the filtrate
  7. washwashed in turn with a saturated sodium bicarbonate aqueous solution
  8. dry with materiala saturated sodium chloride aqueous solution and dried over magnesium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9447219ea02e4cc2b42ebd551b11a356
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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