2-Amino-2-methylpropionitrile → 1-(4-Chloro-3-(trifluoromethyl)phenyl)-5-imino-4,4-dimethyl-4,5-dihydro-1H-imidazol-2-ol

HRID 1979833Notes

Reaction equation

HRID 1979833 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N:10]=[C:11]=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].[NH2:15][C:16]([CH3:20])([CH3:19])[C:17]#[N:18]>>[F:14][C:2]([F:13])([F:1])[C:3]1[CH:4]=[C:5]([N:10]2[C:17](=[NH:18])[C:16]([CH3:20])([CH3:19])[NH:15][C:11]2=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

3

Reactant 2

HCID 880222-Amino-2-methylpropionitrileHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

Product 1

HCID 30540801-(4-Chloro-3-(trifluoromethyl)phenyl)-5-imino-4,4-dimethyl-4,5-dihydro-1H-imidazol-2-ol

Procedure

14.5 g. of 3-trifluoromethyl-4-chlorophenyl-isocyanate and 5.5 g. of α-aminoisobutyronitrile are kept at 100° for 20 minutes. For purification, the viscous oil obtained is chromatographed on 500 g. of silica gel (particle size about 0.06-0.2 mm) using methylene chloride/methanol. The product obtained is crystallized from methylene chloride/petroleum ether. After drying under greatly reduced pressure at 50° for 15 hours, 1-(3-trifluoromethyl-4-chlorophenyl)-5-imino-4,4-dimethyl-2-imidazolidinone, which melts at 148°-149°, is obtained.

Workup

  1. customFor purification
  2. customthe viscous oil obtained
  3. customis chromatographed on 500 g
  4. customThe product obtained
  5. customis crystallized from methylene chloride/petroleum ether
  6. customAfter drying under greatly reduced pressure at 50° for 15 hours

Sources & evidence

ORD record
ord-c041ad8c2b7a4f8f87b70028d192cfb2
Source dataset
uspto-grants-1984_11
Patent number
US04482739

Reaction notes

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