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

HRID 1973916Notes

Reaction equation

HRID 1973916 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-97d9de33e3144dabbfe250317ef1864f
Source dataset
uspto-grants-1976_12
Patent number
US03998970

Reaction notes

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