Hydrochloric Acid → HCID 12177848, compound

HRID 990988Notes

Reaction equation

HRID 990988 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C[O-].[Na+].Br[CH2:16][C:17]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)=[O:18].Cl>CO>[C:19]1([C:17]([C:16]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1]=2[OH:10])=[O:18])[S:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 12177848HCID 12177848, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl thiosalicylate (2.0 g) was added dropwise to a stirred solution of sodium methoxide (1.28 g) in methanol (50 ml) at ambient temperature. The mixture was stirred at ambient temperature for 15 minutes and then a solution of 2-(bromoacetyl)thiophene (2.26 g) in methanol (50 ml) was added dropwise. After the addition was complete the mixture was boiled under reflux for 3 hours, then cooled, and 10% aqueous hydrochloric acid (100 ml) was added. A solid was collected by filtration, dried and then recrystallized from ethanol to give 2-thenoylbenzo[b]thiophene-3-ol.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. filtrationA solid was collected by filtration
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-777a8c1c040d4df2a047b20ba5fde314
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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