Acetic Acid → HCID 9881898, compound

HRID 1017701Notes

Reaction equation

HRID 1017701 reaction equation
C(O[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O)CC.CO[CH:16]([O:20][CH3:21])N(C)C.[C:22]([CH2:24][C:25]([NH2:27])=[S:26])#[N:23].O.[C:29](O)(=O)[CH3:30]>CN(C)C=O>[C:22]([C:24]1[C:25](=[S:26])[NH:27][C:11]([C:10]2[CH:9]=[CH:8][CH:6]=[CH:5][C:16]=2[O:20][CH2:21][CH2:29][CH3:30])=[CH:12][CH:13]=1)#[N:23]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 14162772-CyanoethanethioamideHCID 12715559HCID 12715559, compound

Product 1

HCID 9881898HCID 9881898, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Propoxyacetophenone (2.14 g) and dimethylformamide dimethylacetal (2 ml) were heated together in dimethylformamide (10 ml) at 130° C. for 18 hours. Cyanothioacetamide (1.6 g) was added, heating was continued for 2 hours, and the cool mixture was poured into water (100 ml). The aqueous mixture was neutralized with acetic acid and extracted with ethyl acetate. Evaporation of the extract gave a residue which was purified by medium pressure chromatography (silica, dichloromethane:methanol mixtures) to give a solid, 0.35 g, m.p. 127°-128° C. Recrystallization from aqueous ethanol afforded the pure title compound, 0.22 g, m.p. 130°-131° C.

Workup

  1. temperatureheating
  2. extractionextracted with ethyl acetate
  3. customEvaporation of the extract
  4. customgave a residue which
  5. customwas purified by medium pressure chromatography (silica, dichloromethane:methanol mixtures)
  6. customto give a solid, 0.35 g, m.p. 127°-128° C
  7. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-ecf7afac85534af7a1dd371e08c1152a
Source dataset
uspto-grants-2002_11
Patent number
US06479520B1

Reaction notes

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