Hydrochloric Acid → HCID 9804057, compound

HRID 1589690Notes

Reaction equation

HRID 1589690 reaction equation
C([O:4][C:5]1[C:6]([CH3:35])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28](Cl)[C:29](OCC)=[O:30])=[CH:23][CH:22]=1)([CH2:17][CH3:18])[CH2:9][CH2:8]2)(=O)C.[NH2:36][C:37](N)=[S:38].S1(CCCC1)(=O)=[O:41].Cl>O.COCCO>[CH2:17]([C:10]1([CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH:28]3[S:38][C:37](=[O:41])[NH:36][C:29]3=[O:30])=[CH:25][CH:26]=2)[CH2:9][CH2:8][C:7]2[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([OH:4])[C:6]=2[CH3:35])[O:11]1)[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 20245731HCID 20245731, compound

Product 1

HCID 9804057HCID 9804057, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

2.4 g of ethyl 3-[4-(6-acetoxy-2-ethyl-5,7,8-trimethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate, 494 mg of thiourea and 3 ml of sulfolane were heated under a nitrogen stream for 4.5 hours at 100°-110° C. At the end of this time, 3 ml of ethylene glycol monomethyl ether, 3 ml of water and 1 ml of concentrated hydrochloric acid were added and the resulting mixture was heated for a further 3.5 hours at 96°-98° C. The reaction mixture was then processed as described in Example 1(a) and the resulting crude product, in the form of an oil, was purified by column chromatography, eluted with a 10:1 by volume mixture of benzene and ethyl acetate, to give the title compound.

Workup

  1. temperaturethe resulting mixture was heated for a further 3.5 hours at 96°-98° C
  2. customthe resulting crude product, in the form of an oil, was purified by column chromatography
  3. washeluted with a 10:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-9f22ebc2f7254bacb4abee8b8023eaab
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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