Phosphorus sulfide (P2S5) → 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepine-2-thione

HRID 1580643Notes

Reaction equation

HRID 1580643 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH:9]([CH3:13])[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[S:22])[CH:9]([CH3:13])[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 382377-chloro-3-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Product 1

HCID 126124347-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepine-2-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (0.294 mole), dry pyridine (2300 ml.) and phosphorus pentasulfide (72.4 g.; 0.323 mole) is reflexed under nitrogen for 30 minutes, cooled and concentrated in vacuo. A suspension of the residue in ice water is extracted with methylene chloride. The extract is dried over anhydrous potassium carbonate and concentrated. The residue thus obtained is crystallized from methylene chlorideethanol to give 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepine-2-thione.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionA suspension of the residue in ice water
  4. extractionis extracted with methylene chloride
  5. dry with materialThe extract is dried over anhydrous potassium carbonate
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customis crystallized from methylene chlorideethanol

Sources & evidence

ORD record
ord-98251a72024043dba100ede69d665bbb
Source dataset
uspto-grants-1976_01
Patent number
US03933794

Reaction notes

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