Sulfolane → HCID 19822229, compound

HRID 1030351Notes

Reaction equation

HRID 1030351 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:41])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH:34](Cl)[C:35](OCC)=[O:36])=[CH:29][CH:28]=1)([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[NH2:42][C:43](N)=[S:44].S1(CCCC1)(=O)=[O:47]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([CH3:41])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH:34]3[S:44][C:43](=[O:47])[NH:42][C:35]3=[O:36])=[CH:29][CH:28]=1)([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 2723790ThioureaHCID 19822187HCID 19822187, compound

Product 1

HCID 19822229HCID 19822229, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.1 g of ethyl 3-[4-(6-acetoxy-5,7,8-trimethyl-2-octylchroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 18), 0.35 g of thiourea and 2.5 ml of sulfolane was heated for 7 hours at 120°-130° C. under a nitrogen atmosphere. The reaction mixture was then dissolved in benzene. The benzene solution was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, eluted with a 10:1 by volume mixture of benzene and ethyl acetate, to give the title compound as a slightly yellow, foamy solid.

Workup

  1. temperaturewas heated for 7 hours at 120°-130° C. under a nitrogen atmosphere
  2. washThe benzene solution was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with a 10:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-4f15cb2e1bdd4e4fab51d445f5aa7608
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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