Hydrochloric Acid → HCID 19822223, compound

HRID 1030375Notes

Reaction equation

HRID 1030375 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[C:11]([CH3:40])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH:32](Cl)[C:33](OCC)=[O:34])=[CH:27][CH:26]=1)([CH3:22])[CH2:14][C:13]2=[O:39])=[O:7])([CH3:4])(C)C.[NH2:41][C:42](N)=[S:43].S1(CCCC1)(=O)=[O:46].Cl.[CH3:53][O:54]CCO>O>[O:46]=[C:42]1[NH:41][C:33](=[O:34])[CH:32]([CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH2:23][C:15]3([CH3:22])[CH2:14][C:13](=[O:39])[C:12]4[C:17](=[C:18]([CH3:21])[C:19]([CH3:20])=[C:10]([O:9][CH2:8][C:6]([O:5][CH2:1][CH2:4][O:54][CH3:53])=[O:7])[C:11]=4[CH3:40])[O:16]3)=[CH:26][CH:27]=2)[S:43]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 31347SulfolaneHCID 2723790ThioureaHCID 19822188HCID 19822188, compound

Product 1

HCID 19822223HCID 19822223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 13 g of ethyl 3-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)phenyl]-2-chloropropionate (prepared as described in Preparation 64), 2.6 g of thiourea and 15 ml of sulfolane was heated under a nitrogen stream at 120°-130° C. for 5 hours. 30 ml of 2N aqueous hydrochloric acid and 60 ml of 2-methoxyethanol were added to the resulting mixture, which was then heated at 110° C. for 3 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled from the dried extract, and the residue was purified by silica gel column chromatography (eluted with a 4:1 by volume mixture of benzene and ethyl acetate) to give the title compound.

Workup

  1. temperaturewas heated under a nitrogen stream at 120°-130° C. for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled from the dried
  6. extractionextract
  7. customthe residue was purified by silica gel column chromatography (
  8. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-c780af13d910465b90609d56d7fa9777
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…