Carbon Dioxide → 1-(Methoxymethyl)-3-(1,2,3,4-tetrahydro-1-naphthyl)urea

HRID 1606701Notes

Reaction equation

HRID 1606701 reaction equation
[CH:1]1([NH:11][C:12]([NH2:14])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH2:17]=O.[C:19](=[O:21])=O>CO>[CH3:17][O:21][CH2:19][NH:14][C:12]([NH:11][CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:13]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 13037020(1,2,3,4-Tetrahydronaphthalen-1-yl)urea

Product 1

HCID 213934851-(Methoxymethyl)-3-(1,2,3,4-tetrahydro-1-naphthyl)urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.6 grams (0.04 mole) of (1,2,3,4-tetrahydro-1-naphthyl)urea, 2,0 grams of sodium hydroxide and 2.2 grams of para-formaldehyde in 150 ml. of methanol is stirred at reflux temperature for 10 hours. The reaction mixture is cooled and neutralized with dry ice. The solvent is evaporated at reduced pressure. The residue is treated with water, the mixture filtered, and the filter cake washed with water and dried to give 8.2 grams of product, melting point 124.5° C. to 127.5° C. Recrystallization from methyl isobutyl ketone gives the analytical sample, melting point 136° C. to 138.5° C.

Workup

  1. temperatureat reflux temperature for 10 hours
  2. temperatureThe reaction mixture is cooled
  3. customThe solvent is evaporated at reduced pressure
  4. additionThe residue is treated with water
  5. filtrationthe mixture filtered
  6. washthe filter cake washed with water
  7. customdried

Sources & evidence

ORD record
ord-f61c6c87a2044e8b8d4f21f411ca622e
Source dataset
uspto-grants-1976_04
Patent number
US03953506

Reaction notes

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