4,5,6,7-Tetrahydro-7-oxobenzo[b]thiophen-4-amine hydrochloride → Sulbenox

HRID 263204Notes

Reaction equation

HRID 263204 reaction equation
Cl.[O:2]=[C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]([NH2:12])[CH2:5][CH2:4]1.[O:13]([C:15]#[N:16])[K]>O>[O:2]=[C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]([NH:12][C:15]([NH2:16])=[O:13])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 233477954,5,6,7-Tetrahydro-7-oxobenzo[b]thiophen-4-amine hydrochlorideHCID 178418250HCID 178418250, compound

Product 1

HCID 65473Sulbenox

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The aqueous solution (280 ml.) of (+)-4,5,6,7-tetrahydro-7-oxobenzo[b]thiophen-4-amine hydrochloride from Example 53 is stirred while 40 grams of KOCN in 95 ml. of water is added dropwise. The mixture is warmed to 70° C. for 1.5 hour and cooled to 10° C. The light brown solid is collected and washed well with 700 ml. of water. The product is then stirred with 110 ml. of cold methanol, collected, and washed with 50 ml. of cold methanol to afford 48 grams of the title compound, m.p. 247°-249.5° C. (dec.), [α]D24 =-97.16° (c, 0.14 in methanol).

Workup

  1. temperaturecooled to 10° C
  2. customThe light brown solid is collected
  3. washwashed well with 700 ml
  4. customof cold methanol, collected
  5. washwashed with 50 ml

Sources & evidence

ORD record
ord-9ec13b53c99144ecbcbcf3381ea73987
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

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