1-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-yl)urea → 1-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)urea

HRID 263214Notes

Reaction equation

HRID 263214 reaction equation
[CH3:1][O:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[CH:11]([OH:17])[CH2:10][CH2:9]1)=[O:6]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[C:11](=[O:17])[CH2:10][CH2:9]1)=[O:6]

Participants

4

Reactant 1

HCID 203488891-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-yl)urea

Product 1

HCID 203489901-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-oxobenzo[b]thien-4-yl)ureaYield 90.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

A solution of 1-(methoxymethyl)-3-(4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-yl)urea (0.35 g., 1.37 mmole) in acetone (40 ml.) is treated with manganese dioxide (3.5 g.). After 2 hours stirring the reaction mixture is filtered through celite, the cake washed thoroughly with acetone and the filtrate and washings evaporated to furnish 0.32 g. on 90.7% yield of the title compound as a crystalline solid, m.p. 155°-158° C. Recrystallization from hot acetone affords the analytical sample, m.p. 159°-162° C.

Workup

  1. filtrationis filtered through celite
  2. washthe cake washed thoroughly with acetone
  3. customthe filtrate and washings evaporated
  4. customto furnish 0.32 g

Sources & evidence

ORD record
ord-300b20e8fafb47bb92b6f95edd1120a8
Source dataset
uspto-grants-1979_05
Patent number
US04156670

Reaction notes

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