Acetic acid, (phenylthio)-, ethyl ester → Ethyl 5-dimethylamino-5-benzoyl-2-phenylthio-2,4-pentadienoate

HRID 1074091Notes

Reaction equation

HRID 1074091 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=O)[C:4]([O:6]CC)=S.F[B-](F)(F)F.CN(C)C(C(=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=CC=[N+](C)C.CC[O-].[Na+].C1([S:56]CC(OCC)=O)C=CC=CC=1>C(O)C>[CH3:23][N:2]([CH3:1])[C:3]([C:4](=[O:6])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[CH:9][CH:10]=[C:11]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:12]([O:14][CH2:15][CH3:16])=[S:56]

Participants

6

Reactant 4

HCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 2723922Sodium ethoxideHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioateHCID 86743604N-(3-dimethylamino-3-benzoylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 86743603Ethyl 5-dimethylamino-5-benzoyl-2-phenylthio-2,4-pentadienoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure is as in Example 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-benzoylpropenylidene)-N-methylmethanaminium tetrafluoroborate (5 g), a 2M ethanolic solution of sodium ethylate (7.4 cc) and ethyl (phenylthio)acetate (3.1 g) in ethanol (50 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent, ethyl 5-dimethylamino-5-benzoyl-2-phenylthio-2,4-pentadienoate (4.1 g), m.p. 58° C., is obtained.

Workup

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent

Sources & evidence

ORD record
ord-c661eb4b215945a19d91241901617dcd
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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