Triethylamine → [4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][(4-morpholinyl)thio]amine

HRID 1252675Notes

Reaction equation

HRID 1252675 reaction equation
[N:1]1([S:7]Cl)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:16][C:17]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[Cl:35])[CH:21]=[CH:20][C:18]=1[NH2:19]>C(OCC)C>[Cl:35][C:26]1[CH:27]=[C:28]([C:31]([F:32])([F:34])[F:33])[CH:29]=[CH:30][C:25]=1[O:24][C:22]1[CH:21]=[CH:20][C:18]([NH:19][S:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[C:17]([F:16])[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122977794-Morpholinesulfenyl chlorideHCID 15595105Benzenamine, 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluoro-

Product 1

HCID 15085830[4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl][(4-morpholinyl)thio]amineYield 59.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The compound prepared in Example 5 (3.4 g) was dissolved in diethyl ether (10 ml). The solution was added to a solution of triethylamine (2.2 g) and the compound prepared in Example 1 (6.1 g) in diethyl ether (50 ml) at 15°-20° C. The solution was stirred for 20 minutes, diethyl ether was added (20 ml), the solution was washed with water, and dried. The solvent was removed by evaporation. Column chromatography on silica using 50:50 (v/v) diethyl ether-dichloromethane as eluant yielded the title compound as a brown oil (5 g).

Workup

  1. customat 15°-20° C
  2. washthe solution was washed with water
  3. customdried
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-f9ee56fe44e8463f876ea478c339747b
Source dataset
uspto-grants-1988_05
Patent number
US04745113

Reaction notes

Loading…