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N,N-Dimethylaniline → HCID 12833985, compound

HRID 1660604
Notes
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Reaction equation

HRID 1660604 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 1049PyridineSolvent
HCID 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 (0.42g) 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 oil substance was crystallized by adding ether to give 2,2,2-trichloroethyl 2-methyl-7-[2-(2thienyl)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 oil substance was crystallized
  8. additionby adding ether

Sources & evidence

ORD record
ord-c58555f56c5347ca8c16e76bf79ebdb0
Source dataset
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04308380

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes