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

HRID 652601Notes

Reaction equation

HRID 652601 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-methylcarbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 12.1 g of propyl N-chlorosulphenyl-N-methylcarbamate in 20 ml of diethyl ether was added over 20 minutes to a stirred solution of 18.3 g of 31, and 7 g of triethylamine in 70 ml of the same solvent, the temperature of the mixture 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 200 ml of diethyl ether, washed with water, dried and stripped of solvent. The residue was added to 100 ml of toluene, then the toluene was evaporated under reduced pressure to leave 32, in crude form as a pale brown oil.

Workup

  1. temperaturethe temperature of the mixture 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 ml of toluene
  8. customthe toluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-499f0d7c03a64829a85e0795405a1b0b
Source dataset
uspto-grants-1987_06
Patent number
US04672139

Reaction notes

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