Dimethylformamide → HCID 21490956, compound

HRID 1973912Notes

Reaction equation

HRID 1973912 reaction equation
[OH:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.[H-].[Na+].CN(C)C=O.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:22]([O:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydride2×HCID 23347797HCID 23347797, compound

Product 1

HCID 21490956HCID 21490956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A sample (0.5 g) of 4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-ylacetamide is suspended in 20 ml of dry tetrahydrofuran under a nitrogen atmosphere and the mixture is cooled in an ice bath while 2.1 equivalents or 120 mg of 57% sodium hydride in an oil dispersion is added. The mixture is then stirred at room temperature for an hour and 5 ml of dry N,N-dimethylformamide is added to facilitate dissolution of the sodium hydride. After stirring for an hour, the mixture is cooled in an ice bath and 330 mg of benzyl chloride in 5 ml of dry tetrahydrofuran is added dropwise. The bath is removed and the mixture is stirred at room temperature for several hours. It is then warmed (below boiling point) for an overnight period. Water (25 ml) is carefully added to the reaction mixture and the solvents are stripped off on a rotary evaporator. The residue (yellowish semisolid) is dissolved in dichloromethane and water is added. The dichloromethane layer is collected and the aqueous portion is further extracted with dichloromethane. The combined dichloromethane solutions are washed with 2N hydrochloric acid, water, and dried (magnesium sulfate). The solution is then evaporated in vacuo and the residue is triturated with diethyl oxide. The title product is collected and washed with diethyl oxide to afford 320 mg, m.p. 139° C to 143° C.

Workup

  1. additionis added
  2. stirringAfter stirring for an hour
  3. temperaturethe mixture is cooled in an ice bath
  4. customThe bath is removed
  5. stirringthe mixture is stirred at room temperature for several hours
  6. temperatureIt is then warmed (below boiling point) for an overnight period
  7. additionWater (25 ml) is carefully added to the reaction mixture
  8. customthe solvents are stripped off on a rotary evaporator
  9. dissolutionThe residue (yellowish semisolid) is dissolved in dichloromethane
  10. additionwater is added
  11. customThe dichloromethane layer is collected
  12. extractionthe aqueous portion is further extracted with dichloromethane
  13. washThe combined dichloromethane solutions are washed with 2N hydrochloric acid, water
  14. dry with materialdried (magnesium sulfate)
  15. customThe solution is then evaporated in vacuo
  16. customthe residue is triturated with diethyl oxide
  17. customThe title product is collected
  18. washwashed with diethyl oxide
  19. customto afford 320 mg, m.p. 139° C to 143° C.

Sources & evidence

ORD record
ord-67b36e72d33d447eaf79288cb0e55b7a
Source dataset
uspto-grants-1976_12
Patent number
US03998959

Reaction notes

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