Hydrochloric Acid → HCID 19877648, compound

HRID 1886253Notes

Reaction equation

HRID 1886253 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([SH:12])[CH:6]=[CH:5]2.Br[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].Cl>N1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12][CH2:14][C:15](=[O:23])[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 582216Methyl 6-bromo-5-oxohexanoateHCID 22259560HCID 22259560, compound

Product 1

HCID 19877648HCID 19877648, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
90 °C

Procedure

Into 205 ml (1.16 mmol) of 6-hydroxynaphthalene-2-thiol was charged 5 ml of pyridine, and the mixture was stirred under an ice bath. A solution of 315 mg of methyl 6-bromo-5-oxohexanoate in 2 ml of pyridine was added, and the mixture was stirred under an ice bath for 1 hour. Further, the reaction was carried out at room temperature for 4 hours, by heating to 90° C. for 4 hours, and subsequently stirring was continued at room temperature overnight. The reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate.

Workup

  1. stirringthe mixture was stirred under an ice bath for 1 hour
  2. stirringsubsequently stirring
  3. waitwas continued at room temperature overnight
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-fd9f3472bd424ce0a4512f593af54332
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

Loading…