Pyridine → 2H-1,5-Benzodiazepine-2-thione, 1,3-dihydro-4-phenyl-

HRID 1112582Notes

Reaction equation

HRID 1112582 reaction equation
[C:1]1([C:7]2[CH2:13][C:12](=O)[NH:11][C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].N1C=CC=CC=1>O>[C:1]1([C:7]2[CH2:13][C:12](=[S:20])[NH:11][C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 1777464-Phenyl-3H-1,5-benzodiazepin-2-ol

Product 1

HCID 30329842H-1,5-Benzodiazepine-2-thione, 1,3-dihydro-4-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 23.6 parts of 2,3-dihydro-4-phenyl-1H-1,5-benzodiazepin-2-one and 24.4 parts of phosphorus pentasulfide in 400 parts by volume of pyridine is stirred at reflux temperature for one hour. This solution is then added dropwise with stirring to about 2000 parts by volume of 60° C. warm water. The solid which forms is separated by filtration, washed with water and dried in air overnight. The product thus obtained is recrystallized from ethyl acetate to give, as beige crystals, 2,3-dihydro-4-phenyl-1H-1,5-benzodiazepine-2-thione. This product has the formula ##STR12##

Workup

  1. temperatureat reflux temperature for one hour
  2. additionThis solution is then added dropwise
  3. stirringwith stirring to about 2000 parts by volume of 60° C.
  4. customThe solid which forms is separated by filtration
  5. washwashed with water
  6. customdried in air overnight
  7. customThe product thus obtained
  8. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8cae5124a0ea4ef08e21999caaad123b
Source dataset
uspto-grants-1978_10
Patent number
US04123430

Reaction notes

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