N,N-Dimethylaniline → HCID 12833985, compound

HRID 1764014Notes

Reaction equation

HRID 1764014 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][CH:8]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[N:11]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3C=C[CH:30]=[CH:29][CH:28]=3)[C@H:10]2[S:9]1.CN(C)C1C=CC=CC=1.[S:44]1C=CC=C1CC(Cl)=O>ClCCl.CO.N1C=CC=CC=1>[CH3:7][CH:8]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:20])[Cl:21])=[O:15])[N:11]2[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[S:44][CH:30]=[CH:29][CH:28]=3)[C@H:10]2[S:9]1

Participants

8

Reactant 4

HCID 949N,N-DimethylanilineHCID 24819Phosphorus pentachlorideHCID 1623622-Thiopheneacetyl chlorideHCID 705273932,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 12833985HCID 12833985, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

Pyridine (0.296 g) and phosphorous pentachloride (0.616 g) were added in turn under stirring and cooling at -15° C. to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate (1.12 g), mp 175° to 178° C., in dried dichloromethane (20 ml), and the mixture was stirred for 20 minutes at the same temperature and further for 2 hours at room temperature. To the mixture was added absolute methanol (5 ml) under cooling at -15° C., and then the mixture was stirred for 1 hour at the same temperature. To the mixture were dropwise added in turn dimethylaniline (2.2 g) and a solution of 2-thienylacetyl chloride (0.42 g) in dried dichloromethane (5 ml) at the same temperature, and then the mixture was stirred for 2.5 hours at the same temperature. After the reaction, the reaction mixture was in turn washed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water, and then dried. After the solution was concentrated, the obtained oily substance was crystallized by adding ether to give 2,2,2-trichloroethyl 2-methyl-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylate (750 mg), mp 161° to 162° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 20 minutes at the same temperature and further for 2 hours at room temperature
  2. stirringthe mixture was stirred for 1 hour at the same temperature
  3. customAfter the reaction
  4. washwashed with 5% hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water
  5. customdried
  6. concentrationAfter the solution was concentrated
  7. customthe obtained oily substance was crystallized
  8. additionby adding ether

Sources & evidence

ORD record
ord-d1568615924f4f69a86095eb6903cc65
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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