Benzyl Bromide → HCID 21455231, compound

HRID 1606447Notes

Reaction equation

HRID 1606447 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:13])[C:4]2=[CH:14][S:15][CH:16]=[C:3]12.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3]2=[CH:16][S:15][CH:14]=[C:4]2[C:5]1=[O:13])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 21455231HCID 21455231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.35 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one, 65 mg. of 57% sodium hydride-mineral oil dispersion and 0.3 ml. of benzylbromide in 10 ml. of dimethylformamide is stirred at room temperature for 3 hours, quenched by dropwise addition of water, diluted with 100 ml. of water and extracted several times with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated under reduced pressure to give a yellow oil which is chromatographed on silica gel with benzene-methanol (19:1) to give an oil which crystallizes on trituration with acetonitrile. Recrystallization from methanol-water gives off-white crystals, m.p. 137°-138.5°C.

Workup

  1. additionA mixture of 0.35 g
  2. customquenched by dropwise addition of water
  3. additiondiluted with 100 ml
  4. extractionof water and extracted several times with chloroform
  5. dry with materialThe chloroform solution is dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil which
  8. customis chromatographed on silica gel with benzene-methanol (19:1)
  9. customto give an oil which
  10. customcrystallizes on trituration with acetonitrile
  11. customRecrystallization from methanol-water
  12. customgives off-white crystals, m.p. 137°-138.5°C.

Sources & evidence

ORD record
ord-357156f2e5304ffca3f741549704f3c4
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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