Trifluoroacetic acid → HCID 19389041, compound

HRID 1110317Notes

Reaction equation

HRID 1110317 reaction equation
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=[C:10]([S:33]([CH3:35])=[O:34])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:35][S:33]([C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=1)=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54174940HCID 54174940, compound

Product 1

HCID 19389041HCID 19389041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.5 g (2.86 mmol) of 3-(methylsulfinyl)-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester and 1.1 ml (14.3 mmol) of trifluoroacetic acid in 50 ml of methylene chloride was kept at room temperature for 41 hours. The solvent was removed at reduced pressure, the residue was treated with NaHCO3 solution and the product was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to a solid which was recrystallized from methylene chloride-hexane to give 1.13 g (94% yield), mp 104°-106°, of 3-(methylsufinyl)-5-(octadecyloxy)benzenamine.

Workup

  1. customThe solvent was removed at reduced pressure
  2. additionthe residue was treated with NaHCO3 solution
  3. extractionthe product was extracted with methylene chloride
  4. extractionThe dried extract
  5. concentrationwas concentrated at reduced pressure to a solid which
  6. customwas recrystallized from methylene chloride-hexane
  7. customto give 1.13 g (94% yield), mp 104°-106°

Sources & evidence

ORD record
ord-bca7c74fac324e4badef5b0c3ba659ec
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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