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

HRID 259338Notes

Reaction equation

HRID 259338 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+]>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

4

Reactant 2

HCID 65473Sulbenox2×HCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same manner as described in reducing the (-)-4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-ylurea, (+)- 4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-ylurea is reduced with NaBH4 to afford isomer B of the title compound, m.p. 216°-217° C. (dec.), [α]D25.5 = + 18.51° (c, 2.11 in methanol). This isomer is 95% pure by high pressure liquid chromatography. Isomer A of the title compound is also purified by high pressure liquid chromatography as a 90-95% pure material, m.p. 160°-164° C. (dec.), [α]D24.5 = -91.03° (c, 2.2 in methanol). The cis and trans configurations for isomers A and B have not been determined unequivocally.

Sources & evidence

ORD record
ord-0bd297284613456c97f50feade4faf6e
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

Loading…