1,2-Ethanedione, 1,2-bis(4-chlorophenyl)- → 4,5-Bis-(4-chlorophenyl)-5-hydroxy-2-thioxo-3-pyrroline-3-carbonitrile

HRID 745216

Reaction equation

HRID 745216 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=O)=[O:9])=[CH:4][CH:3]=1.[C:19]([CH2:21][C:22]([NH2:24])=[S:23])#[N:20]>N1CCCCC1.C(Cl)(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([OH:9])[NH:24][C:22](=[S:23])[C:21]=2[C:19]#[N:20])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 189461,2-Ethanedione, 1,2-bis(4-chlorophenyl)-HCID 14162772-Cyanoethanethioamide

Product 1

HCID 132362254,5-Bis-(4-chlorophenyl)-5-hydroxy-2-thioxo-3-pyrroline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6212ChloroformSolvent

Procedure

A suspension of 22.3 g. 4,4'-dichlorobenzil, 6.5 g. 2-cyanothioacetamide, 20 drops of piperidine and 200 ml. chloroform is stirred for 20 hours at ambient temperature. The yellow precipitate obtained is filtered off with suction, well washed with chloroform and dried. There are obtained 22.0 g. of the desired compound in the form of yellow crystals; m.p. 213° C. (decomp.).

Workup

  1. additionA suspension of 22.3 g
  2. customThe yellow precipitate obtained
  3. filtrationis filtered off with suction
  4. washwell washed with chloroform
  5. customdried
  6. customThere are obtained 22.0 g

Sources & evidence

ORD record
ord-506c9676fa5f4cd0ba78dad36495d7f2
Source dataset
uspto-grants-1986_07
Patent number
US04598076

Linked notes

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