Hydrogen Sulfide → Thionordiazepam

HRID 649261

Reaction equation

HRID 649261 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](OP(N3CCOCC3)(N3CCOCC3)=O)[CH2:9][N:8]=[C:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[CH:33]=1.[SH2:34]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[S:34])[CH2:9][N:8]=[C:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[CH:33]=1

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 149078867-chloro-2-di-(morpholino)phosphinyloxy-5-phenyl-3H-1,4-benzodiazepin

Product 1

HCID 826706Thionordiazepam

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 245 mg. (0.5 mmole) of 7-chloro-2-di-(morpholino)phosphinyloxy-5-phenyl-3H-1,4-benzodiazepine in 10 ml. of tetrahydrofuran containing 0.5 ml. of triethylimine at room temperature was introduced a stream of hydrogen sulfide gas until tlc indicated that all the starting material was consumed (15 minutes). Tetrahydrofuran was evaporated. The residue was partitioned between methylene chloride and water. The methylene chloride layer was dried and evaporated. Crystallization of the residue from methanol yielded, in two crops, a product having a melting point of 243°-245°.

Workup

  1. customwas consumed (15 minutes)
  2. customTetrahydrofuran was evaporated
  3. customThe residue was partitioned between methylene chloride and water
  4. dry with materialThe methylene chloride layer was dried
  5. customevaporated
  6. customCrystallization of the residue from methanol
  7. customyielded, in two crops

Sources & evidence

ORD record
ord-3003a7854e9646f68410136383523365
Source dataset
uspto-grants-1988_04
Patent number
US04739049

Linked notes

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