Ethyl Acetate → HCID 10546273, compound

HRID 1899094Notes

Reaction equation

HRID 1899094 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[CH:9]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)(=O)C>C1C=CC=CC=1.C(OCC)C>[CH3:25][N:2]([CH2:3][C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([S:16][CH3:17])=[CH:14][CH:15]=2)[CH:9]=1)[CH3:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10523272HCID 10523272, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10546273HCID 10546273, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N,N-dimethyl-5-(4-fluorophenyl)-4-[4-(methylthio)phenyl]thiophene-2-carboxamide (1.95 g) in benzene (15 ml) was added dropwise to an ice-cooled mixture of lithium aluminum hydride (0.27 g) in diethyl ether (10 ml). The mixture was refluxed for 9 hours. To the mixture was added dropwise 4N sodium hydroxide solution. Ethyl acetate was added, and the mixture was filtered. The filtrate was washed with water, dried and evaporated. The oily residue (2 g) was purified by column chromatography on silica gel (20 g) eluting with a mixture of toluene and ethyl acetate (2:1) to give a yellow oil of N,N-dimethyl-5-(4-fluorophenyl)-4-[4-(methylthio)phenyl]-2-thenylamine (1.5 g).

Workup

  1. temperaturecooled
  2. temperatureThe mixture was refluxed for 9 hours
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with water
  5. customdried
  6. customevaporated
  7. customThe oily residue (2 g) was purified by column chromatography on silica gel (20 g)
  8. washeluting with a mixture of toluene and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-5b6354b73a194b00a725f7824bb1561c
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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