1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 2-[2-[3(4-Chloro-3-(trifluoromethyl)phenyl]ureido]-4-(trifluoromethyl)phenoxy]-4,5-dichlorobenzenesulfonic acid, ammonium salt

HRID 1416350Notes

Reaction equation

HRID 1416350 reaction equation
[NH2:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:6]=1[S:13]([OH:16])(=[O:15])=[O:14].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][C:27]=1[C:35]([F:38])([F:37])[F:36]>N1C=CC=CC=1>[NH4+:1].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:34])[NH:1][C:2]2[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:3]=2[O:4][C:5]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:6]=2[S:13]([O-:16])(=[O:15])=[O:14])=[CH:28][C:27]=1[C:35]([F:36])([F:37])[F:38]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 152858292-(2-Amino-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid

Product 1

HCID 154073252-[2-[3(4-Chloro-3-(trifluoromethyl)phenyl]ureido]-4-(trifluoromethyl)phenoxy]-4,5-dichlorobenzenesulfonic acid, ammonium salt

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(2-amino-4-trifluoromethylphenoxy)-4,5-dichlorobenzenesulfonic acid (2 g, 4.8 mmol) and 4chloro-3-trifluoromethylphenyl isocyanate (1.11 g, 5 mmol) in pyridine (20 mL) was stirred under argon for 72 hours (hereinafter h). The solvent was evaporated and the residue was flash chromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide) to give the tide compound. 1H NMR (400 MHz, CD3OD) δ 8.61 (d, 1H), 8.08 (s, 1H), 7.95 (d, 1H), 7.60 (dd, 1H), 7.43 (d, 1H), 7.30-7.36 (m, 2H), 7.10 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. customchromatographed (silica gel, methylene chloride/ethanol/ammonium hydroxide)
  3. customto give the tide compound

Sources & evidence

ORD record
ord-1e6f4541c0b549e19212595a5805b86a
Source dataset
uspto-grants-1999_06
Patent number
US05912270

Reaction notes

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