Phosphorus sulfide (P2S5) → 5-(2-Chlorophenyl)-7-ethyl-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione

HRID 1658530Notes

Reaction equation

P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[C:23]2[CH:32]=[C:31]([CH2:33][CH3:34])[S:30][C:24]=2[NH:25][C:26](=O)[CH2:27][N:28]=1>N1C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[C:23]2[CH:32]=[C:31]([CH2:33][CH3:34])[S:30][C:24]=2[NH:25][C:26](=[S:2])[CH2:27][N:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Diphosphorus pentasulphide (32 g) is added to a solution of 40 g of 5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e] [1,4]diazepin-2-one on 20 ml of pyridine, and the resulting mixture is stirred at 60° C for 1 hour, and then allowed to cool. Then, the reaction mixture is poured into 2 liters of ice water under cooling, and the precipitate is collected by suction filtration, washed well with water and dissolved in chloroform. The chloroform solution is washed with an aqueous sodium hydrogen carbonate solution and then with water, dried over sodium sulfate, and then concentrated under reduced pressure. The residue is recrystallized from a mixture of ethanol and chloroform to give 31.4 g of 5-o-chlorophenyl-7-ethyl-1,2-dihydro-3H-thieno[2,3-e] [1,4] diazepine-2-thione as yellow crystals, melting at 198°-199° C with decomposition.

Workup

temperatureto cool
temperatureunder cooling
filtrationthe precipitate is collected by suction filtration
washwashed well with water
dissolutiondissolved in chloroform
washThe chloroform solution is washed with an aqueous sodium hydrogen carbonate solution
dry with materialwith water, dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue is recrystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record: ord-5cfc6dd4723b46d8b0ecb675f0aba07f
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03965111

Reaction notes

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