Phosphorus sulfide (P2S5) → 2(3H)-Benzoxazolethione, 3-methyl-

HRID 1271684Notes

Reaction equation

HRID 1271684 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:13]>>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[S:13]

Participants

3

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 308462-Benzoxazolinone, 3-methyl-

Product 1

HCID 1395382(3H)-Benzoxazolethione, 3-methyl-Yield 80%

Conditions

Temperature
140 °C

Procedure

3-Methyl-3H-benzoxazol-2-one (2.0 g, 13.4 mmol) was treated with diphosphorus pentasulphide (4.0 g, 18 mmol). The mixture was heated to 140° C. for 2 hours with vigorous stirring. The solid was cooled and then extracted with toluene (2×50 ml). The toluene extract was evaporated in vacuo and the residue partitioned between ethyl acetate (2×10 ml) and water (20 ml). The organic phases were combined and dried over magnesium sulfate. The volatiles were removed in vacuo to provide the desired compound as a white solid (1.77 g, 80%).

Workup

  1. temperatureThe solid was cooled
  2. extractionextracted with toluene (2×50 ml)
  3. extractionThe toluene extract
  4. customwas evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate (2×10 ml) and water (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-007692ad50d549af82118cf99cfc994f
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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