2,6-Xylyl isocyanate → HCID 13137046, compound

HRID 1702142Notes

Reaction equation

HRID 1702142 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][NH:5][C:4](=[S:7])[NH:3]1.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[N:17]=[C:18]=[O:19]>CN(C)C=O>[CH3:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH3:9])[C:11]=1[NH:17][C:18]([N:5]1[CH2:6][C:2]([CH3:8])([CH3:1])[NH:3][C:4]1=[S:7])=[O:19]

Participants

4

Reactant 2

HCID 987872,6-Xylyl isocyanateHCID 30325022-Imidazolidinethione, 4,4-dimethyl-

Product 1

HCID 13137046HCID 13137046, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 39.0 g (0.3 M) 4,4-dimethylimidazolidine-2-thione, 44.2 g (0.3 M) 2,6-dimethylphenyl isocyanate and 100 ml dimethylformamide was refluxed with stirring for 24 hours. After cooling to room temperature, the solution was filtered from a small amount of insoluble solid and poured into 300 ml water with efficient stirring. The precipitated product was filtered, washed well with water, and dried in vacuo. Yield 62.6 g, mp 228°-231° C. Recrystallization from 600 ml of boiling methanol yielded 46 g of N-(2,6-dimethylphenyl)-4,4-dimethyl-2-thioxo-1-imidazolidinecarboxamide as white crystalline product, mp 241.5°-243° C. A small sample was recrystallized from benzene to give an analytical sample, mp 245.5°-246° C.

Workup

  1. temperaturewas refluxed
  2. filtrationthe solution was filtered from a small amount of insoluble solid
  3. additionpoured into 300 ml water with efficient stirring
  4. filtrationThe precipitated product was filtered
  5. washwashed well with water
  6. customdried in vacuo
  7. customRecrystallization from 600 ml of boiling methanol

Sources & evidence

ORD record
ord-519e2a03ac34440788c0284429d76778
Source dataset
uspto-grants-1983_04
Patent number
US04380548

Reaction notes

Loading…