Water → HCID 135848416, compound

HRID 262979Notes

Reaction equation

HRID 262979 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]2[CH:20]=[CH:19][S:18][C:12]=2[NH:13][C:14](=O)[CH2:15][N:16]=1)([O-:3])=[O:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].O>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]2[CH:20]=[CH:19][S:18][C:12]=2[NH:13][C:14](=[S:22])[CH2:15][N:16]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 135734194HCID 135734194, compound

Product 1

HCID 135848416HCID 135848416, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

15.7 g (0.055 mol) of 1,3-dihydro-5-(o-nitrophenyl)-2H-thieno[2,3-e]-1,4-diazepin-2-one are warmed to 60° C. in 40 ml of absolute pyridine and there are added with vigorous stirring 15.7 g of finely powdered phosphorus pentasulphide. The mixture is stirred for a further 1.5 hours at this temperature, subsequently poured on to 500 g of ice and 500 ml of water with vigorous stirring and stirred for 2 hours. The resulting precipitate is filtered under a vacuum and washed with a large amount of water. The precipitate is suspended in water and shaken out thoroughly with 500 ml of methylene chloride each time. After drying, the organic phase is evaporated under reduced pressure and the residue refluxed with a small amount of chloroform. After completion of the crystallization in a refrigerator, there is obtained 1,3-dihydro-5-(o-nitrophenyl)-2H-thieno[2,3-e]-1,4-diazepine-2-thione which, after recrystallization from absolute methanol, melts at 207°-209° C.

Workup

  1. additionthere are added
  2. stirringwith vigorous stirring
  3. stirringstirred for 2 hours
  4. filtrationThe resulting precipitate is filtered under a vacuum
  5. washwashed with a large amount of water
  6. stirringshaken out thoroughly with 500 ml of methylene chloride each time
  7. customAfter drying
  8. customthe organic phase is evaporated under reduced pressure
  9. temperaturethe residue refluxed with a small amount of chloroform
  10. customAfter completion of the crystallization in a refrigerator

Sources & evidence

ORD record
ord-793413d28ee444a6a973e5a32a03ae79
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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