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

HRID 259347Notes

Reaction equation

HRID 259347 reaction equation
[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.[OH-].[Na+].[CH2:17]=O.[C:19](=[O:21])=O>O.CO>[CH3:17][O:21][CH2:19][NH:14][C:12]([NH:11][CH:5]1[C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:13]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 20348930N-(7-Hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)urea

Product 1

HCID 203488891-(Methoxymethyl)-3-(4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-yl)ureaYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,5,6,7-tetrahydro-7-hydroxybenzo[b]-thien-4-yl urea (4 g., 18.87 mmole), sodium hydroxide (0.969 g., 24.22 mmole), paraformaldehyde (1.038 g., 34.6 mmole) and methanol (94 ml.) is stirred and heated at reflux under a nitrogen atmosphere for 23 hours. The mixture is allowed to cool and excess solid carbon dioxide is added. Evaporation in vacuo affords a solid which is stirred with water (50 ml.) for 2 hours, filtered and air dried to furnish 3.16 g., of the title compound (65% yield) m.p. 157°-159° C. dec. Recrystallization from hot acetone gives the analytical specimen 160°-161° C. dec.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for 23 hours
  3. temperatureto cool
  4. customEvaporation in vacuo
  5. customaffords a solid which
  6. filtrationfiltered
  7. customair dried
  8. customto furnish 3.16 g

Sources & evidence

ORD record
ord-c07dea7a052f4d93995d1111bc725121
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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