Hydrochloric Acid → HCID 13488878, compound

HRID 1589684Notes

Reaction equation

HRID 1589684 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]([CH2:18][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)([CH3:17])[CH2:9][CH2:8]2)(=O)C.[NH2:36][C:37](N)=[S:38].S1(CCCC1)(=O)=[O:41].Cl>COCCO.O>[OH: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]([CH2:18][CH2:19][O:20][C:21]1[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]=1)([CH3:17])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 20245680HCID 20245680, compound

Product 1

HCID 13488878HCID 13488878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

1.6 g of ethyl 3-{4-[2-(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)ethoxy]phenyl}-2-chloropropionate, 300 mg of thiourea and 2 ml of sulfolane were heated at 110°-115° C. for 3 hours under a nitrogen stream. A mixture of 4 ml of water, 2 ml of ethylene glycol monomethyl ether and 1 ml of concentrated hydrochloric acid was then added and the whole mixture was heated at 95°-97° C. for 4.5 hours. The mixture was then treated as described in Example 1(a), except that the crude product, in the form of an oil, was purified by column chromatography through silica gel, eluted with a 10:1 by volume mixture of benzene and ethyl acetate, to give the title compound, melting at 152°-154° C.

Workup

  1. additionwas then added
  2. temperaturethe whole mixture was heated at 95°-97° C. for 4.5 hours
  3. additionThe mixture was then treated
  4. customwas purified by column chromatography through silica gel
  5. washeluted with a 10:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-03c4e9a101ad48b0bf54f12678137cd0
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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