Phosphorus sulfide (P2S5) → 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

HRID 1485374Notes

Reaction equation

HRID 1485374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=O)[NH:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[S:22])[NH:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 709793321-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 867184911-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-oneYield 49.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(4-chlorophenyl)-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (2.00 g, 7.0 mmol) and P2S5 (1.87 g, 8.4 mmol) in pyridine (40 ml) was refluxed, with stirring for 1 h under N2 atmosphere. The solvent was evaporated in vacuo to afford a residue. The residue was purified by column chromatography (silica-gel, DCM:MEOH=40:1) to give 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1.05 g, 49%). LRMS (M+H+) m/z: calcd 302.03. found 302.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto afford a residue
  3. customThe residue was purified by column chromatography (silica-gel, DCM:MEOH=40:1)

Sources & evidence

ORD record
ord-0b76623e65384c32bb28eec3d301b559
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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