Dimethylformamide → HCID 20392225, compound

HRID 1863179Notes

Reaction equation

HRID 1863179 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[CH3:16]N(C)C=O.[H-].[Na+].CCC[CH2:26][CH2:27][CH3:28]>>[CH3:16][C:27](=[CH2:26])[CH2:28][N:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[NH:5][C:4]2=[CH:3][S:2][CH:1]=[C:10]2[C:9]1=[O:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 24758Sodium hydrideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392225HCID 20392225, compound

Procedure

An 11.8 g. portion of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 175 ml. of dimethylformamide is stirred. A 2.8 g. portion of 50% sodium hydride in mineral oil is treated with hexane to remove the mineral oil and then added to the reaction mixture. After 2 hours of stirring, 6.7 g. (7.2 ml.) of methallyl chloride is added. The mixture is stirred overnight and poured into ice-water. The mixture is extracted with four 250 ml. portions of methylene chloride. The extracts are combined, washed with water, dried over sodium sulfate, filtered and concentrated to dryness. The crude product is dissolved in 10 ml. of 40% methylene chloride in hexane and chromatographed on an alumina column, eluting with the same solvent. Those fractions which contain the desired product as determined by thin layer chromatography are combined and concentrated to give the crude product. This product is heated to solution in 25 ml. of benzene, filtered and the solid which forms is collected, washed with hexane and dried giving the desired product, mp. 161°-163° C.

Workup

  1. customto remove the mineral oil
  2. additionadded to the reaction mixture
  3. addition(7.2 ml.) of methallyl chloride is added
  4. stirringThe mixture is stirred overnight
  5. additionpoured into ice-water
  6. extractionThe mixture is extracted with four 250 ml
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. dissolutionThe crude product is dissolved in 10 ml
  12. customof 40% methylene chloride in hexane and chromatographed on an alumina column
  13. washeluting with the same solvent
  14. concentrationconcentrated
  15. customto give the crude product
  16. temperatureThis product is heated to solution in 25 ml
  17. filtrationof benzene, filtered
  18. customthe solid which forms is collected
  19. washwashed with hexane
  20. customdried

Sources & evidence

ORD record
ord-ab13d58d468b437587ed15d660108124
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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