Dimethylamine → HCID 174802, compound

HRID 917982Notes

Reaction equation

HRID 917982 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:5]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:18][NH:19][CH3:20].[CH2:21]=O>CN(C)C=O>[CH3:1][C:2]1[O:3][C:4]2[CH:15]=[C:14]([CH2:18][N:19]([CH3:21])[CH3:20])[C:13]([OH:16])=[C:12]([Cl:17])[C:5]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 122247863-Benzofurancarboxylic acid, 4-chloro-5-hydroxy-2-methyl-, ethyl ester

Product 1

HCID 174802HCID 174802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.9 g of 2-methyl-3-carbethoxy-4-chloro-5-hydroxybenzofuran, 2.6 ml of a 33 percent aqueous solution of dimethylamine and 0.6 ml of 36 percent Formalin in 12 ml of dimethylformamide is refluxed at a temperature of 100° to 105° for 8 hours and then cooled to ambient temperature. The precipitated crystals are filtered off, washed with water and dried in order to yield 0.75 g of crystalline 2-methyl-3-carbethoxy-4-chloro-hydroxy-6-dimethylaminomethylbenzofuran. An additional 0.4 g of crystals is obtained from the parent solution by dilution with water. The total yield is 1.15 g (50%); m.p., 130°-131°C (from alcohol). Mixed melting of the product crystals with a specimen from Example 1a gave no depression of the melting point.

Workup

  1. filtrationThe precipitated crystals are filtered off
  2. washwashed with water
  3. customdried in order

Sources & evidence

ORD record
ord-4ba3764374f144ec926854d8cbc85848
Source dataset
uspto-grants-1976_07
Patent number
US03968237

Reaction notes

Loading…