1,1'-Carbonyldiimidazole → 3-(2,4-Difluorophenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

HRID 394437Notes

Reaction equation

HRID 394437 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[CH:12]1[N:16]=[CH:15][N:14]([C:17](N2C=NC=C2)=[O:18])[CH:13]=1.CNC(NC)=[S:27]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17](=[O:18])[N:14]([CH3:13])[C:15](=[S:27])[N:16]([CH3:12])[C:10]1=[O:11]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5932582,4-Difluorophenyl isocyanateHCID 2723631N,N'-Dimethylthiourea

Product 1

HCID 114603213-(2,4-Difluorophenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
62.5 °C

Procedure

31 g of 2,4-difluorophenyl isocyanate and 64.9 g of carbodiimidazole were added in succession to 20.8 g of N,N′-dimethylthiourea in 500 ml of toluene and 1 ml of triethylamine. This mixture was stirred first for 3 hours at 60-65° C. and then for 12 hours at 80-85° C. After cooling to room temperature, the mixture was washed three times with 100-ml-portions of water, and the organic phase was dried over sodium sulfate. After distillation of the low-boiling fractions, 48 g of the desired product of melting point 156-159° C. remained.

Workup

  1. waitfor 12 hours at 80-85° C
  2. temperatureAfter cooling to room temperature
  3. washthe mixture was washed three times with 100-ml-portions of water
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. distillationAfter distillation of the low-boiling fractions, 48 g of the desired product of melting point 156-159° C.

Sources & evidence

ORD record
ord-a74141f264694a1f9434ba9eaebfea61
Source dataset
uspto-grants-2003_08
Patent number
US06602825B1

Reaction notes

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