Dicyclohexylcarbodiimide → 1-[4-(Thiomorpholino)butyryloxy]-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d] pyran

HRID 267351Notes

Reaction equation

HRID 267351 reaction equation
[OH:1][C:2]1[C:11]2[C:10]3[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=1.Cl.[S:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])[CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[S:29]1[CH2:30][CH2:31][N:32]([CH2:35][CH2:36][CH2:37][C:38]([O:1][C:2]2[C:11]3[C:10]4[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=4[C:8]([CH3:17])([CH3:18])[O:7][C:6]=3[CH:5]=[C:4]([CH:19]([CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:20])[CH:3]=2)=[O:39])[CH2:33][CH2:34]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 362763-(1,2-dimethylheptyl)-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo(b,d)pyran-1-olHCID 70633382gamma-Thiomorpholinobutyric acid hydrochloride

Product 1

HCID 537268201-[4-(Thiomorpholino)butyryloxy]-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d] pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.0 g. (10.8 mmole) of 1-hydroxy-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[ b,d] pyran, 2.4 g. (10.8 mmole) of γ-thiomorpholinobutyric acid hydrochloride, 2.38 g. (11.5 mmole) of dicyclohexylcarbodiimide and 250 ml. of methylene chloride was stirred and heated at reflux for 18 hours. After cooling the reaction mixture, the byproduct of dicyclohexylurea was removed by suction filtration. The solvent was evaporated to give a red-brown residue which was chromatographed using 90 g. of activated magnesium silicate (60-100 mesh) and chloroform as the solvent system. The fractions were monitored by thin layer chromatography, and the appropriate fractions were combined and evaporated to give 1.0 g. of a light yellow oil. The material was pure by thin layer chromatography, and the infrared and nuclear magnetic resonance spectra were in agreement with the designated structure.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureheated
  3. temperatureat reflux for 18 hours
  4. temperatureAfter cooling the reaction mixture
  5. customthe byproduct of dicyclohexylurea was removed by suction filtration
  6. customThe solvent was evaporated
  7. customto give a red-brown residue which
  8. customwas chromatographed
  9. customevaporated
  10. customto give 1.0 g

Sources & evidence

ORD record
ord-1d42ce80a6b4417581a7d0d82cf085a4
Source dataset
uspto-grants-1976_03
Patent number
US03941782

Reaction notes

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