Hydrochloric Acid → HCID 9891469, compound

HRID 1589691Notes

Reaction equation

HRID 1589691 reaction equation
C([O:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30](Cl)[C:31](OCC)=[O:32])=[CH:25][CH:24]=1)([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:8]2)(=O)C.[NH2:38][C:39](N)=[S:40].S1(CCCC1)(=O)=[O:43].Cl>O.COCCO>[OH:4][C:5]1[C:6]([CH3:37])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH:30]3[S:40][C:39](=[O:43])[NH:38][C:31]3=[O:32])=[CH:27][CH:28]=1)([CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 2723790ThioureaHCID 20245598HCID 20245598, compound

Product 1

HCID 9891469HCID 9891469, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

1.99 g of ethyl 3-[4-(6-acetoxy-2-isobutyl-5,7,8-trimethylchroman-2-ylmethoxy)phenyl]-2-chloropropionate, 0.42 g of thiourea and 2.1 g of sulfolane were reacted under a nitrogen stream at 125°-150° C. for 3.5 hours. At the end of this time, 15 ml of ethylene glycol monomethyl ether, 4 ml of water and 2 ml of concentrated hydrochloric acid were added and the mixture was reacted for a further 3.5 hours at 96°-98° C. The reaction mixture was then treated as described in Example 1(a) and the resulting crude product, in the form of an oil, was purified by column chromatography through silica gel, eluted with a 5:1 by volume mixture of hexane and ethyl acetate, to give the title compound.

Workup

  1. customthe mixture was reacted for a further 3.5 hours at 96°-98° C
  2. additionThe reaction mixture was then treated
  3. customthe resulting crude product, in the form of an oil, was purified by column chromatography through silica gel
  4. washeluted with a 5:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-753c17ae561347c29f6d01ca9f64cf67
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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