Acetic Acid → HCID 23035227, compound

HRID 1709969Notes

Reaction equation

HRID 1709969 reaction equation
[CH3:1][O:2][C:3]1[C:25]([O:26][CH3:27])=[CH:24][C:6]2[S:7][C:8]([C:10](N3CCOCC3)([CH:13]([CH3:17])[CH2:14][C:15]#[N:16])C#N)=[CH:9][C:5]=2[CH:4]=1.C(O)(=[O:30])C>O>[CH3:1][O:2][C:3]1[C:25]([O:26][CH3:27])=[CH:24][C:6]2[S:7][C:8]([C:10](=[O:30])[CH:13]([CH3:17])[CH2:14][C:15]#[N:16])=[CH:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 23035259HCID 23035259, compound

Product 1

HCID 23035227HCID 23035227, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(5,6-dimethoxy-benzo[b]thien-2-yl)-3-methyl-2-(4-morpholinyl)-pentanedinitrile (7.4 g), glacial acetic acid (37.5 ml) and water (12.5 ml) was stirred and heated at reflux under an atmosphere of nitrogen. After 45 min. the reaction mixture was cooled and poured into crushed ice (200 g). The ice was allowed to melt and the resultant precipitate was filtered and dried at 65° C. under vacuum to give 4-(5,6-dimethoxybenzo[b]thien-2-yl)-3-methyl-4-oxo-butane nitrile as a pale yellow solid (5.2 g). A portion crystallized from dichloromethane/diethyl ether had m.p. 148°-150° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under an atmosphere of nitrogen
  3. temperatureAfter 45 min. the reaction mixture was cooled
  4. additionpoured
  5. filtrationthe resultant precipitate was filtered
  6. customdried at 65° C. under vacuum

Sources & evidence

ORD record
ord-f600eda9994647a09e1af7651292f604
Source dataset
uspto-grants-1990_08
Patent number
US04952571

Reaction notes

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