Ethanol → HCID 136062352, compound

HRID 991002Notes

Reaction equation

HRID 991002 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[C:13](OC)(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[SH:16].C[O-].[Na+].C(O)C>Cl>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([C:8]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13]=2[OH:21])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 986544-(Bromoacetyl)benzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 136062352HCID 136062352, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-cyanophenacyl bromide (3.0 g), methyl thiosalicylate (2.25 g), sodium methoxide (1.52 g) and ethanol (100 ml) was boiled under reflux for 3.5 hours. The mixture was cooled and diluted with 2M hydrochloric acid (100 ml). A precipitate was collected by filtration and recrystallized from ethanol to give 2-(4-cyanobenzoyl)-3-hydroxybenzo[b]thiophene.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationA precipitate was collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-044cd68a96864c66960bec72c066491c
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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