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

HRID 436131Notes

Reaction equation

HRID 436131 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.N1C=CC=CC=1.ClN1C(=O)CCC1=O>O>[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

5

Reactant 3

HCID 1049PyridineHCID 31398ChlorosuccinimideHCID 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 962WaterSolvent

Procedure

To a suspension of 3.8 g. of 1,3,4,9-tetrahydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 15 ml. of dry pyridine is added, in portions, a total of 2.18 g. of N-chlorosuccinimide. The resulting solution is heated on a steam bath for 15 minutes, cooled and diluted with water. The solid is collected and recrystallized from methanol, to give a tan solid, m.p. 224°-225° C. (dec.).

Workup

  1. additionTo a suspension of 3.8 g
  2. temperatureThe resulting solution is heated on a steam bath for 15 minutes
  3. temperaturecooled
  4. customThe solid is collected
  5. customrecrystallized from methanol
  6. customto give a tan solid, m.p. 224°-225° C. (dec.)

Sources & evidence

ORD record
ord-0d787f726bd144aca98702dae85e0727
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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