Triethylamine → Propyl N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]thio]-N-methylcarbamate

HRID 255604Notes

Reaction equation

HRID 255604 reaction equation
Cl[S:2][N:3]([CH3:10])[C:4](=[O:9])[O:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:18]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[Cl:30])[CH:16]=[CH:15][C:13]=1[NH2:14].C(N(CC)CC)C>C(OCC)C>[Cl:30][C:21]1[CH:22]=[C:23]([C:26]([F:27])([F:29])[F:28])[CH:24]=[CH:25][C:20]=1[O:19][C:17]1[CH:16]=[CH:15][C:13]([NH:14][S:2][N:3]([CH3:10])[C:4](=[O:9])[O:5][CH2:6][CH2:7][CH3:8])=[C:12]([F:11])[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15595105Benzenamine, 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluoro-HCID 20183881propyl N-chlorosulphenyl-N-methylcarbamate

Product 1

HCID 20183886Propyl N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl]amino]thio]-N-methylcarbamateYield 97.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of propyl N-chlorosulphenyl-N-methylcarbamate (12.1g) in diethyl ether (20 ml) was added to a stirred solution of the compound of Example 1 (18.3 g) and triethylamine (7 g) in the same solvent (70 ml) over 20 minutes, the temperature being maintained at 15°-20° C. with cooling. Stirring was continued at room temperature for a further 11/2 hours. The reaction mixture was then diluted with diethyl ether (200 ml), washed with water, dried and stripped of solvent. The residue was added to 100 mls toluene, and the toluene was removed under reduced pressure to leave 26.5 g of the desired product in crude form as a brown oil.

Workup

  1. temperaturethe temperature being maintained at 15°-20° C.
  2. temperaturewith cooling
  3. customwas continued at room temperature for a further 11
  4. custom2 hours
  5. washwashed with water
  6. customdried
  7. additionThe residue was added to 100 mls toluene
  8. customthe toluene was removed under reduced pressure

Sources & evidence

ORD record
ord-3b1936addd6447218d64579828b8f981
Source dataset
uspto-grants-1987_10
Patent number
US04698365

Reaction notes

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