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

HRID 2351539Notes

Reaction equation

HRID 2351539 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 solutionwas 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 chromatogrpahy 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-4a29b51441144cc298ec7642f6f5aff3
Source dataset
uspto-grants-1989_10
Patent number
US04873327

Reaction notes

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