Acetone → HCID 20362892, compound

HRID 1679424Notes

Reaction equation

HRID 1679424 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([N:14]([CH2:17]C)CC)C.[CH:19]([N:22]1[C:26](=[O:27])[CH2:25]NC1=O)([CH3:21])[CH3:20].CC(C)=[O:31]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:25]([C:17](=[O:31])[NH2:14])[C:26](=[O:27])[N:22]([CH:19]([CH3:20])[CH3:21])[C:10]2=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 8471TriethylamineHCID 944603,5-Dichlorophenyl isocyanateHCID 5680853-(1-Methylethyl)-2,4-imidazolidinedione

Product 1

HCID 20362892HCID 20362892, compound

Conditions

Temperature
20 °C

Procedure

A solution of 3,5-dichlorophenyl isocyanate (71.5 g.) in acetone (250 cc.), and triethylamine (38.4 g.) are added successively, whilst stirring, to a solution of 3-isopropyl-hydantoin (56.8 g.) in acetone (250 cc.). The temperature of the reaction mixture rises gradually from 25° C to 50° C over the course of 20 minutes and then again drops, whilst a copious precipitate forms. The reaction mixture is stirred for a further 5 hours at a temperature of about 20° C. The precipitate is filtered off, washed with acetone (2 × 50 cc.) and then dried under reduced pressure. 1-(3,5-Dichlorophenyl)-carbamoyl-3-isopropyl-hydantoin (100 g.) melting at 200° C, is thus obtained.

Workup

  1. customrises gradually from 25° C to 50° C over the course of 20 minutes
  2. filtrationThe precipitate is filtered off
  3. washwashed with acetone (2 × 50 cc.)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4eea92eacb154ef2a1de00594c15c163
Source dataset
uspto-grants-1978_03
Patent number
US04080473

Reaction notes

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