Chloroform → 5-Hydroxy-4,5-bis-(4-methoxyphenyl)-2-thioxo-3-pyrroline-3-carbonitrile

HRID 745215

Reaction equation

HRID 745215 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=[O:10])=[CH:5][CH:4]=1.[C:21]([CH2:23][C:24]([NH2:26])=[S:25])#[N:22].C(Cl)(Cl)Cl>N1CCCCC1.O>[OH:10][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:26][C:24](=[S:25])[C:23]([C:21]#[N:22])=[C:11]1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 710434,4'-DimethoxybenzilHCID 14162772-Cyanoethanethioamide

Product 1

HCID 132362265-Hydroxy-4,5-bis-(4-methoxyphenyl)-2-thioxo-3-pyrroline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

16.5 g. 4,4'-Dimethoxybenzil, 6.0 g. cyanothioacetamide and 15 drops of piperidine were boiled for 2 hours in 200 ml. chloroform on a water separator. The yellow precipitate obtained was filtered off with suction, washed with some chloroform and dried at 80° C. and 0.1 mm.Hg for 12 hours. The desired product is obtained in a yield of 17.6 g. in the form of yellow crystals; m.p. 193° C. (decomp.).

Workup

  1. customThe yellow precipitate obtained
  2. filtrationwas filtered off with suction
  3. washwashed with some chloroform
  4. customdried at 80° C.

Sources & evidence

ORD record
ord-5d8aedaf79514e46ad9aa677b0d80ce6
Source dataset
uspto-grants-1986_07
Patent number
US04598076

Linked notes

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