2,6-Difluorobenzoyl isocyanate → HCID 15451883, compound

HRID 1637249Notes

Reaction equation

HRID 1637249 reaction equation
[F:1][C:2]1[C:8]([Cl:9])=[C:7]([O:10][CH:11]([CH3:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[C:6]([Cl:20])=[CH:5][C:3]=1[NH2:4].[F:21][C:22]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:23]=1[C:24]([N:26]=[C:27]=[O:28])=[O:25]>ClCCCl>[F:21][C:22]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:23]=1[C:24]([NH:26][C:27]([NH:4][C:3]1[CH:5]=[C:6]([Cl:20])[C:7]([O:10][CH:11]([CH3:19])[C:12]([F:18])([F:17])[C:13]([F:15])([F:16])[F:14])=[C:8]([Cl:9])[C:2]=1[F:1])=[O:28])=[O:25]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 9798100HCID 9798100, compound

Product 1

HCID 15451883HCID 15451883, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

200 mg of 2-Fluoro-3,5-dichloro-4-(1-methyl-2,2,3,3,3-pentafluoropropoxy)aniline was stirred in 15 mL 1,2-dichloroethane as 118 mg 2,6-difluorobenzoyl isocyanate in 5 mL 1,2-dichloroethane was added. The mixture was heated under reflux for 30 minutes before lowering heat and stirring overnight. The mixture was then concentrated to half volume and chilled to give 120 mg of 1-(2,6-Difluorobenzoyl)-3-[2-fluoro-3,5-dichloro-4-(1-methyl-2,2,3,3,3-pentafluoropropoxy)phenyl]urea as a white solid. 1H NMR: 10.60 (s, 1H), 9.46 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.54 (m, 1H), 7.08 (t, J=8.7 Hz, 2H), 5.11 (m, 1H), 1.43 (d, J=6.7 Hz, 3H). MS: 524 m/z. IR: 1699(s), 1469(s).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturebefore lowering heat
  5. concentrationThe mixture was then concentrated to half volume
  6. temperaturechilled

Sources & evidence

ORD record
ord-0a92942853a54f8081ff13a6846f35b4
Source dataset
uspto-grants-2000_03
Patent number
US06040345

Reaction notes

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