Acetic Acid → Sulbenox

HRID 259333Notes

Reaction equation

HRID 259333 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]([NH:10][C:11]([NH2:13])=[O:12])[CH2:7][CH2:8][CH2:9][C:2]1=2.C(O)(=[O:16])C>O>[O:16]=[C:9]1[C:2]2[S:1][CH:5]=[CH:4][C:3]=2[CH:6]([NH:10][C:11]([NH2:13])=[O:12])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13036998N-(4,5,6,7-Tetrahydro-1-benzothiophen-4-yl)urea

Product 1

HCID 65473Sulbenox

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 6 grams of 4,5,6,7-tetrahydrobenzo[b]thien-4-ylurea is dissolved in 375 ml. of 50% aqueous acetic acid and 75 grams of ceric ammonium nitrate is added in portions over a 10 minute period with stirring at 25° C. to 35° C. The pale-orange solution is stirred for another 5 minutes and 100 ml. of water is added. The solution is extracted twice with ethyl acetate (450 ml. and 350 ml.) and the combined extracts are washed with 100 ml. of water. The organic extract is evaporated to dryness in vacuo and the brown residue is crystallized from methanol to afford 2.37 grams of 4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-ylurea, melting point 237° C. to 238° C. dec. Recrystallization from methanol affords purified product, melting point 245° C. to 246° C. dec.

Workup

  1. stirringThe pale-orange solution is stirred for another 5 minutes
  2. extractionThe solution is extracted twice with ethyl acetate (450 ml. and 350 ml.)
  3. washthe combined extracts are washed with 100 ml
  4. extractionThe organic extract
  5. customis evaporated to dryness in vacuo
  6. customthe brown residue is crystallized from methanol

Sources & evidence

ORD record
ord-9f18a7aab6ab4582b6d1a2bf02a0535e
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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