Phosphorus sulfide (P2S5) → HCID 86718495, compound

HRID 1485399Notes

Reaction equation

HRID 1485399 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12](=O)[NH:11][C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>N1C=CC=CC=1>[CH2:1]([N:8]1[C:14](=[O:15])[CH2:13][C:12](=[S:22])[NH:11][C:10]2[CH:17]=[CH:18][CH:19]=[CH:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 57263819HCID 57263819, compound

Product 1

HCID 86718495HCID 86718495, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-benzyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (160 mg, 0.60 mmol) and P2S5 (140 mg, 0.63 mmol) in 20 mL of pyridine was heated to reflux and stirred for 1 h under N2 atmosphere. The solvent was evaporated in vacuo, the residue was purified by prep-TLC (DCM:MeOH=50:1) to give 1-benzyl-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (50 mg, 30%). 1H NMR (300 MHz, DMSO): δ 3.74 (q, J=12.3 Hz, J=12.3 Hz, 1H), 5.12 (q, J=15.6 Hz, J=15.9 Hz, 1H), 7.03-7.06 (m, 2H), 7.17-7.27 (m, 6H), 7.48 (d, J=7.5 Hz, 1H).

Workup

  1. temperatureto reflux
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by prep-TLC (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-cf7a614fd1084a76b530e30b7b0be2a0
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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