Methanol → HCID 54191689, compound

HRID 1730749Notes

Reaction equation

HRID 1730749 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([S:10]([CH2:12][C:13]([OH:15])=[O:14])=[O:11])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.[CH:24]1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1>[CH3:24][O:14][C:13](=[O:15])[CH2:12][S:10]([CH:8]([C:6]1[CH:5]=[CH:4][C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:2]([F:1])[CH:7]=1)[CH3:9])=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 20348775HCID 20348775, compound

Product 1

HCID 54191689HCID 54191689, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 1.53 gm (5 millimols) of [1-(2-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 161°-163° C, in 15 ml of benzene was admixed with 0.24 gm (7.5 millimols) of methanol, and then a solution of 1.25 gm (6 millimols) of dicyclohexyl-carbodiimide in 5 ml of benzene was added. After stirring for one hour, the precipitated dicyclohexylurea was suction-filtered off, the filtrate was evaporated, and the residue was purified by chromatography on 300 gm of silicagel with cyclohexane/ethyl acetate = 1/4. Yield: 1.4 gm (87.6% of theory); oil, Rf -value: 0.5 on carrier 1 with cyclohexane/ethyl acetate = 1/4.

Workup

  1. filtrationthe precipitated dicyclohexylurea was suction-filtered off
  2. customthe filtrate was evaporated
  3. customthe residue was purified by chromatography on 300 gm of silicagel with cyclohexane/ethyl acetate = 1/4

Sources & evidence

ORD record
ord-f7868b48ea4648f9b36f9fcf5c3ccb8c
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

Loading…