Sulfur → 4,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 436130Notes

Reaction equation

HRID 436130 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[CH2:14][S:15][CH2:16][C:3]1=2.[S]>C(Cl)(Cl)Cl>[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

Participants

4

Reactant 2

HCID 5362487SulfurHCID 125216321,3,4,9-tetrahydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one

Product 1

HCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.5 g. of 1,3,4,9-tetrahydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 0.5 g. of sulfur is fused at 160° C. ± 5 for 1 hour. The fusion mixture is slurried with chloroform and filtered. The filtrate is chromatographed on silica gel with benzene:methanol 9:1 to give a solid, which is recrystallized from methanol-water to give a tan solid, m.p. 224°-225° C. (dec.).

Workup

  1. additionA mixture of 0.5 g
  2. filtrationfiltered
  3. customThe filtrate is chromatographed on silica gel with benzene:methanol 9:1
  4. customto give a solid, which
  5. customis recrystallized from methanol-water
  6. customto give a tan solid, m.p. 224°-225° C. (dec.)

Sources & evidence

ORD record
ord-6fa6c95a255e476f96f40dca3d58a551
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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