Hydrochloric Acid → HCID 15230518, compound

HRID 1742479Notes

Reaction equation

HRID 1742479 reaction equation
Br[CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:27]([Cl:28])=[C:26]([O:29]C(=O)C)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[O:33]C(=O)C)=[CH:13][CH:12]=1)[C:3](OCCCC)=[O:4].[NH2:37][C:38](N)=[S:39].S1(CCCC1)(=O)=[O:42].Cl.O=O>O.COCCO>[Cl:28][C:27]1[C:26](=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:33])[C:18]=1[O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:2]2[S:39][C:38](=[O:42])[NH:37][C:3]2=[O:4])=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 977OxygenHCID 31347SulfolaneHCID 2723790ThioureaHCID 19009259HCID 19009259, compound

Product 1

HCID 15230518HCID 15230518, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.8 g of butyl 2-bromo-3-[4-(1,4-diacetoxy-3-chloro-2-naphthyloxy)phenyl]propiona te (prepared as described in Preparation 18), 1 g of thiourea and 10 ml of sulfolane was heated at 120° C. for 5 hours under an atmosphere of nitrogen. At the end of this time, 20 ml of ethylene glycol monomethyl ether and 10 ml of 2N aqueous hydrochloric acid were added to the mixture in the presence of atmospheric oxygen, and the resulting mixture was heated at 100° C. for 6 hours. The reaction mixture was then poured into water, after which it was extracted with benzene. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was then removed from the extract by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of benzene and ethyl acetate as the eluent. About 2.4 g of the title compound were obtained by recrystallization from a mixture of tetrahydrofuran and hexane as crystals, melting at 250°-252° C.

Workup

  1. temperaturethe resulting mixture was heated at 100° C. for 6 hours
  2. extractionafter which it was extracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then removed from the
  6. extractionextract by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through silica gel
  8. additionby volume mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-282961a10bac4c29b83c0b86e22ce69e
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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