Dimethylformamide dimethyl acetal → Thiourea, [(dimethylamino)methylene]phenyl-

HRID 1077092Notes

Reaction equation

HRID 1077092 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:13][N:14]([CH3:16])[CH:15]=[N:10][C:8](=[S:9])[NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 676454Phenylthiourea

Product 1

HCID 3711213Thiourea, [(dimethylamino)methylene]phenyl-

Procedure

6.1 G. PHENYLTHIOUREA AND 4.3 G. DIMETHYL FORMAMIDE DIMETHYLACETAL WERE SUSPENDED IN 100 ML. OF BENZENE WITH ~ 100 MG OF P-TOLUENE SULFURIC ACID AND THE MIXTURE DISTILLED THROUGH A 6 PLATE DISTILLING COLUMN. The methanol-benzene azeotrope, bp 57°C, came off rapidly. After the bp rose to 80°C, the mixture was cooled and the product crystallized from the benzene. The yield was 6.3 g of solid m.p. 131°-138°C which was triturated with ether to give 6 g m.p. 139°-143°C.

Workup

  1. distillationOF BENZENE WITH ~ 100 MG OF P-TOLUENE SULFURIC ACID AND THE MIXTURE DISTILLED THROUGH A 6 PLATE
  2. distillationDISTILLING COLUMN
  3. customrose to 80°C
  4. temperaturethe mixture was cooled
  5. customthe product crystallized from the benzene
  6. customThe yield was 6.3 g of solid m.p. 131°-138°C which was triturated with ether
  7. customto give 6 g m.p. 139°-143°C.

Sources & evidence

ORD record
ord-717c468e5c264a21b799e57d4ba79416
Source dataset
uspto-grants-1976_05
Patent number
US03959368

Reaction notes

Loading…