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 255607Notes

Reaction equation

HRID 255607 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 2,6-difluorobenzoyl isocyanate (2.0 g) in dry methylene chloride (10 ml) was added rapidly to a stirred solution of the compound of Example 2 (4.5 g) in the same solvent (20 ml) at room temperature. After stirring for 4 hours the solvent was removed under reduced pressure, and the residue was purified by chromatography (2x) on silica, using first methylene chloride and then diethyl ether as eluant. The product thus obtained was finally purified by crystallisation from diethyl ether/light petroleum affording colourless crystals (4.5 g) melting at 98°-99° C.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue was purified by chromatography (2x) on silica
  3. customThe product thus obtained
  4. customwas finally purified by crystallisation from diethyl ether/light petroleum affording colourless crystals (4.5 g) melting at 98°-99° C.

Sources & evidence

ORD record
ord-6c75eb4752574d63be955161ff5dec3c
Source dataset
uspto-grants-1987_10
Patent number
US04698365

Reaction notes

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