Water → N-(7-Hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

HRID 263205Notes

Reaction equation

HRID 263205 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.[BH4-].[Na+].O>C(O)C.CO>[OH:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([NH:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 65473SulbenoxHCID 4311764Sodium borohydride

Product 1

HCID 20348930N-(7-Hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

In 2.5 liters of ethanol, 34.85 grams of (-)-4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-ylurea is stirred and 9.8 grams of NaBH4 is added. The mixture is stirred overnight at room temperature, 1400 ml. of water is added, and after stirring for 0.5 hour the ethanol is evaporated in vacuo. The mixture is cooled and 25-30 ml. of acetic acid is added until no more foaming occurs. The mixture is stirred for 0.75 hour, filtered to collect the first crop and this solid is washed with water and air dried. This solid is recrystallized from acetone and then from acetone/methanol to give 6.75 g. of isomer B of the title compound, m.p. 211°-213° C. (dec.), [α]D25.5 =-23.23° (c, 3.11 in methanol). This material contains 92% isomer B and 8% isomer A when assayed by high pressure liquid chromatography.

Workup

  1. customis evaporated in vacuo
  2. temperatureThe mixture is cooled
  3. additionof acetic acid is added until no more foaming
  4. stirringThe mixture is stirred for 0.75 hour
  5. filtrationfiltered
  6. customto collect the first crop
  7. washthis solid is washed with water and air
  8. customdried
  9. customThis solid is recrystallized from acetone
  10. customfrom acetone/methanol to give 6.75 g

Sources & evidence

ORD record
ord-663f3aa0705e487c8e296c4ab33fc0c1
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

Loading…