Acetic Acid → Sulbenox

HRID 1701208Notes

Reaction equation

HRID 1701208 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-cc906af1b7e04ac8b464f29667d5e65c
Source dataset
uspto-grants-1980_03
Patent number
US04191830

Reaction notes

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