Hydrochloric Acid → HCID 178473073, compound

HRID 1074070Notes

Reaction equation

HRID 1074070 reaction equation
CN(C)[C:3](=[CH:9][CH:10]=[C:11]([S:23][CH3:24])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.C([OH:29])C>>[CH3:21][N:20]([CH3:22])[C:17]1[CH:18]=[CH:19][C:14]([C:12](=[O:13])[C:11]([S:23][CH3:24])=[CH:10][CH:9]=[C:3]([OH:29])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86743594HCID 86743594, compound

Product 1

HCID 178473073HCID 178473073, compound

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 4, starting with ethyl 2-dimethylamino-6-(4-dimethylaminophenyl)-5-methylthio-6-oxo-2,4-hexadienoate (5.5 g), 12N aqueous hydrochloric acid solution (38 cc) and ethanol (50 cc). The mixture is heated to boiling for 5 minutes, and is then cooled to a temperature of approximately 20° C. After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (60:40 by volume), ethyl 6-(4-dimethylaminophenyl)-2-hydroxy-5-methylthio-6-oxo-2,4-hexadienoate (3.9 g) is obtained in the form of a brown oil (Rf=0.2; support: silica gel; eluent: cyclohexane/ethyl acetate 60:40 by volume).

Workup

  1. temperatureThe mixture is heated
  2. customAfter purification by chromatography on a silica column
  3. additionwith a mixture of cyclohexane and ethyl acetate (60:40 by volume)

Sources & evidence

ORD record
ord-8b5a3922b3fa41afb7858949eb453574
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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