Methylamine → 2,6-bis(hydroxymethyl)pyridine bis(N-methylcarbamate)

HRID 34984

Reaction equation

HRID 34984 reaction equation
[CH3:1][NH2:2].ClC[O:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][O:17][C:18]([O:20]CCl)=[O:19])[N:11]=1)=[O:7]>>[CH3:1][NH:2][C:18](=[O:19])[OH:20].[CH3:1][NH:2][C:6](=[O:5])[OH:7].[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[N:11]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 147495552,6-Bis(chloromethyloxy-carbonyloxymethyl)pyridine

Product 1

HCID 236159442,6-bis(hydroxymethyl)pyridine bis(N-methylcarbamate)Yield 97%

Conditions

Temperature
10 °C

Procedure

3.15 ml of methanolic methylamine solution (containing 33.6% by weight, i.e. 0.024 moles, of methylamine) are added to a solution of 1.3 g (0.004 moles) of 2,6-bis(chloromethyloxy-carbonyloxymethyl)pyridine (prepared as described in Example 1) at about 0° C. under cooling at such a rate that the temperature is maintained at 10° C. or lower. A crystalline precipitate is separated. After completing the addition, 5 ml of water are added to the mixture which is then cooled to 2° to 5° C. The precipitate is separated by filtration and dried to give 0.97 g of the title compound, m.p.: 132°-135° C. The yield is 97% as calculated for 2,6-bis(hydroxymethyl)pyridine. The 2,6-bis(hydroxymethyl)pyridine bis(N-methylcarbamate) content of the thus-obtained product is 98% based on the spectrophotometric determination.

Workup

  1. temperatureunder cooling at such a rate that the temperature
  2. customA crystalline precipitate is separated
  3. additionthe addition, 5 ml of water
  4. additionare added to the mixture which
  5. temperatureis then cooled to 2° to 5° C
  6. customThe precipitate is separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-b038f647bb27431aaf565d4a607bf1a4
Source dataset
uspto-grants-1988_08
Patent number
US04764613

Linked notes

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