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

HRID 1701213Notes

Reaction equation

HRID 1701213 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-2a9d414efec94b42bc2ab2b66d1d0fe1
Source dataset
uspto-grants-1980_03
Patent number
US04191830

Reaction notes

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