Water → 2-Nitrodibenzo[b,f][1,4]thiazepine-11(10H)-thione

HRID 1082071Notes

Reaction equation

HRID 1082071 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[NH:10][C:9](=O)[C:8]=2[CH:19]=1)([O-:3])=[O:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[NH:10][C:9](=[S:21])[C:8]=2[CH:19]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 14118983HCID 14118983, compound

Product 1

HCID 233620162-Nitrodibenzo[b,f][1,4]thiazepine-11(10H)-thioneYield 154.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Nitro-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one (0.27 g) was dissolved in toluene (20 ml). Phosphorus pentasulphide (0.22 g) was added to the solution and the whole was stirred under reflux for 4 hours, then cooled and left overnight. Addition of water (40 ml) and separation of the phases gave, after evaporation of the dried organic layer, a yellow solid which was purified by column chromatography on silica gel and recrystallisation from ethanol to give the product as yellow needles (0.22 g, m/s. M+ =288).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. customgave
  4. customafter evaporation of the dried organic layer
  5. customa yellow solid which was purified by column chromatography on silica gel and recrystallisation from ethanol

Sources & evidence

ORD record
ord-9fd2558cfbc14c89b000be9be4cee454
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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