Hydrochloric Acid → HCID 19822251, compound

HRID 1030352Notes

Reaction equation

HRID 1030352 reaction equation
C([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]([O:37]CC)=O)=[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)C.[NH2:42][C:43](N)=[S:44].S1(CCCC1)(=O)=[O:47].Cl>O.COCCO>[OH: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:28]=[CH:29][C:30]([CH2:33][CH:34]3[S:44][C:43](=[O:47])[NH:42][C:35]3=[O:37])=[CH:31][CH:32]=1)([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 19822187HCID 19822187, compound

Product 1

HCID 19822251HCID 19822251, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

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. A mixture of 3.6 ml of 2N aqueous hydrochloric acid and 5 ml of ethylene glycol monomethyl ether was then added to the reaction mixture, after which it was heated for a further 5 hours at 85°-90° C. The reaction mixture was then poured into water and extracted with benzene. The benzene extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography, using a 10:1 by volume mixture of benzene and ethyl acetate as eluent, to give the title compound as a slightly yellow, foamy solid.

Workup

  1. additionwas then added to the reaction mixture
  2. temperatureafter which it was heated for a further 5 hours at 85°-90° C
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. additionby volume mixture of benzene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-e9cc86a9da364a2cac15265b69db5d30
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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