Thionyl Chloride → HCID 178443552, compound

HRID 2379010Notes

Reaction equation

HRID 2379010 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:28]=[CH:27][C:17]([C:18]([NH:20][C@@H:21]([CH:24]([CH3:26])[CH3:25])[CH2:22][OH:23])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].S(Cl)(Cl)=O>C(=O)([O-])[O-].[K+].[K+]>[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:18]3[O:23][CH2:22][C@H:21]([CH:24]([CH3:25])[CH3:26])[N:20]=3)=[CH:27][CH:28]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178443555HCID 178443555, compound

Product 1

HCID 178443552HCID 178443552, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1.05 g of 4-(trans-4-heptylcyclohexyl)-N-[(S)-2-hydroxy-1-isopropylethyl)benzamide in 40 ml of acetenitrile was treated dropwise with 0.7 ml of thionyl chloride at 0° C. and while gassing with nitrogen. The reaction mixture was stirred at 0° C. overnight, poured into 100 ml of saturated potassium carbonate solution and then extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 50 ml of saturated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 2:1) and recrystallization from acetone at -25° C. gave pure (S)-2-[4-(trans-4-heptylcyclohexyl)phenyl]-4-isopropyl-2-oxazoline with m.p. (C-I) 51° C. and cl.p. (S-I) 46° C.

Workup

  1. extractionextracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases were washed twice with 50 ml of saturated sodium chloride solution each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationsubsequently concentrated
  6. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 2:1) and recrystallization from acetone at -25° C.

Sources & evidence

ORD record
ord-4ab1ed5deb7e49fc8b8d469b42aba53b
Source dataset
uspto-grants-1994_11
Patent number
US05360577

Reaction notes

Loading…