Tributylphosphine → HCID 13711424, compound

HRID 986413Notes

Reaction equation

HRID 986413 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:13]S[C:11](=[O:14])[N:10]=1.[Cl:15][C:16]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20]([Cl:27])=[CH:19][C:17]=1[NH2:18].C(P(CCCC)CCCC)CCC>ClCCl>[Cl:15][C:16]1[C:22]([C:23]([F:25])([F:26])[F:24])=[CH:21][C:20]([Cl:27])=[CH:19][C:17]=1[NH:18][C:11]([NH:10][C:9](=[S:13])[C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:14]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 13648922HCID 13648922, compoundHCID 136718552,5-Dichloro-3-(trifluoromethyl)aniline

Product 1

HCID 13711424HCID 13711424, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(2,6-difluorophenyl)-1,2,4-dithiazole-3-one (0.9 g) in 20 ml of dichloromethane was added dropwise a solution of 2,5-dichloro-3-trifluoromethylaniline (0.9 g) and tributylphosphine (0.8 g) in 10 ml of dichloromethane under ice-cooling and the solution was stirred for 30 minutes at room temperature. The dichloromethane was then distilled off under reduced pressure and to the residue was added ligroin. The precipitated crystal was filtered and the crystal was washed with ligroin to obtain the desired product 1.3 g. (d.p. 176°-177° C.)

Workup

  1. temperaturecooling
  2. distillationThe dichloromethane was then distilled off under reduced pressure and to the residue
  3. additionwas added ligroin
  4. filtrationThe precipitated crystal was filtered
  5. washthe crystal was washed with ligroin

Sources & evidence

ORD record
ord-17607399c4f54285805b5f047cb349cb
Source dataset
uspto-grants-1987_12
Patent number
US04713396

Reaction notes

Loading…