2,6-Difluorobenzoyl isocyanate → HCID 9870860, compound

HRID 1637248Notes

Reaction equation

HRID 1637248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:19])[C:8]=1[O:9][CH:10]([CH3:18])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[NH2:5].[F:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:22]=1[C:23]([N:25]=[C:26]=[O:27])=[O:24]>ClCCCl>[F:20][C:21]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:22]=1[C:23]([NH:25][C:26]([NH:5][C:4]1[CH:3]=[C:2]([Cl:1])[C:8]([O:9][CH:10]([CH3:18])[C:11]([F:16])([F:17])[C:12]([F:14])([F:15])[F:13])=[C:7]([Cl:19])[CH:6]=1)=[O:27])=[O:24]

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 154518823,5-Dichloro-4-(1-methyl-2,2,3,3,3-pentafluoropropoxy)aniline

Product 1

HCID 9870860HCID 9870860, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.0 of 3,5-Dichloro-4-(1-methyl-2,2,3,3,3-pentafluoropropoxy)aniline was placed in a flask to which was added 15 mL of 1,2-dichloroethane. With stirring, 0.62 g 2.6-difluorobenzoyl isocyanate was added all at once to the mixture. The mixture was warmed to near reflux for one hour then cooled to room temperature and stirred overnight. It was then concentrated under vacuum to give 2.30 g crude product. The product was recrystallized from toluene, giving 208 mg of 1-(2,6-difluorobenzoyl)-3-[3,5-dichloro-4-(1-methyl-2,2,3,3,3-pentafluoropropoxy)phenyl]urea. 1H NMR: 10.59 (s, 1H) 9.58 (s, 1H), 7.34 (m, 3H), 7.07 (t, J=8.4 Hz,2H), 5.09 (m, 1H). MS: 506 m/z. IR:1746(s), 1710(s), 1539(s), 1470(m).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto near reflux for one hour
  3. stirringstirred overnight
  4. concentrationIt was then concentrated under vacuum
  5. customto give 2.30 g crude product
  6. customThe product was recrystallized from toluene

Sources & evidence

ORD record
ord-6f8e1f9171e24251be49028e019052f3
Source dataset
uspto-grants-2000_03
Patent number
US06040345

Reaction notes

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