2,6-Difluorobenzoyl isocyanate → HCID 15595108, compound

HRID 1731791Notes

Reaction equation

HRID 1731791 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25][N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[C:20]([F:33])[CH:19]=1>C(OCC)C>[Cl:14][C:15]1[CH:37]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:35]=[CH:34][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([S:25][N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:8])=[C:20]([F:33])[CH:19]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 15595106HCID 15595106, compound

Product 1

HCID 15595108HCID 15595108, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.6 g of 2,6-difluorobenzoyl isocyanate in 15 ml of diethyl ether was added over 30 seconds to 5.4 g of 38C. The solution was stirred at ambient temperature for 2.5 hours after which a slight precipitate formed. 50 ml of petroleum ether was added, and the resulting suspension was cooled in a freezer (-5° to 0° C.) for 3 hours. The precipitate which formed was filtered off and recrystallised from a 1:1 v:v mixture of diethyl ether and petroleum ether, to give 2.3 g of 38, as white crystals, m.p.: 118°-121° C.

Workup

  1. customformed
  2. temperaturethe resulting suspension was cooled in a freezer (-5° to 0° C.) for 3 hours
  3. customThe precipitate which formed
  4. filtrationwas filtered off
  5. customrecrystallised from a 1:1 v
  6. additionv mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-980b3c25be7e4864840a55f4036af70e
Source dataset
uspto-grants-1986_11
Patent number
US04623658

Reaction notes

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