Benzyl Bromide → 4-Benzyl-4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 436148Notes

Reaction equation

HRID 436148 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2=[CH:15][S:16][CH:17]=[C:6]2[C:5]1=[O:18].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH3:3])[C:5](=[O:18])[C:6]2=[CH:17][S:16][CH:15]=[C:7]12)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 203922504,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 214552424-Benzyl-4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 0.18 g. of 57% sodium hydride-mineral oil dispersion in 25 ml. of dimethylformamide is added 0.92 g. of 4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]-benzodiazepin-10-one and 0.8 ml. of benzyl bromide. The mixture is stirred at room temperature for 3.5 hours, quenched by dropwise addition of water, diluted with 200 ml. of water and extracted several times with chloroform. The chloroform extracts are dried over magnesium sulfate and concentrated under reduced pressure to give an amber oil, which crystallizes on trituration with methanol. Recrystallization from aqueous methanol and then from ethyl acetate gives off-white crystals, m.p. 151.5°-153° C.

Workup

  1. customquenched by dropwise addition of water
  2. additiondiluted with 200 ml
  3. extractionof water and extracted several times with chloroform
  4. dry with materialThe chloroform extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an amber oil, which
  7. customcrystallizes on trituration with methanol
  8. customRecrystallization from aqueous methanol
  9. customfrom ethyl acetate gives off-white crystals, m.p. 151.5°-153° C.

Sources & evidence

ORD record
ord-05b0cccd54df49a48cfb9ec126cdfbcc
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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