2,6-Difluorobenzoyl isocyanate → Propyl 4-[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]-7-(2,6-difluorophenyl)-2-methyl-5,7-dioxo-3-thia-2,4,6-triazaheptanoate

HRID 1731788Notes

Reaction equation

HRID 1731788 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:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25][N:26]([CH3:33])[C:27](=[O:32])[O:28][CH2:29][CH2:30][CH3:31])=[C:20]([F:34])[CH:19]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=[CH:35][C:16]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([C:7](=[O:8])[NH:6][C:4]([C:3]2[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=2[F:13])=[O:5])[S:25][N:26]([CH3:33])[C:27]([O:28][CH2:29][CH2:30][CH3:31])=[O:32])=[C:20]([F:34])[CH:19]=1

Participants

4

Reactant 2

HCID 27333692,6-Difluorobenzoyl isocyanateHCID 20183886Propyl N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]thio]-N-methylcarbamate

Product 1

HCID 20183878Propyl 4-[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]-7-(2,6-difluorophenyl)-2-methyl-5,7-dioxo-3-thia-2,4,6-triazaheptanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g of 2,6-difluorobenzoyl isocyanate in 10 ml of dry methylene chloride was added rapidly to a stirred solution of 4.5 g of 32 in 20 ml of the same solvent at room temperature. After stirring for 4 hours the solvent was removed under reduced pressure, and the residue was purified by chromatography twice on silica, using first methylene chloride and then diethyl ether as eluent. The product thus obtained was finally purified by crystallization from diethyl ether/light petroleum to give 35, as colourless crystals, m.p.: 98°-99° C.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue was purified by chromatography twice on silica
  3. customThe product thus obtained
  4. customwas finally purified by crystallization from diethyl ether/light petroleum

Sources & evidence

ORD record
ord-0b11db0bdc09406d826579c8fc44cdf6
Source dataset
uspto-grants-1986_11
Patent number
US04623658

Reaction notes

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