Methylamine → HCID 13298527, compound

HRID 1580975

Reaction equation

[CH3:1][NH2:2].[Br:3][CH:4]([CH2:16][Br:17])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](O)=[O:14])=[N:11][CH:12]=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH3:1][NH:2][C:13](=[O:14])[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH:4]([Br:3])[CH2:16][Br:17])=[CH:12][N:11]=1

Participants

Conditions

Temperature: 8 °C

Procedure

According to the same method as Example 1 with cooling 30% aqueous methylamine solution (100 ml) was added to the chloroform solution (200 ml) of acid chloride prepared from 10 g of 5-(3,4-dibromobutyl)picolinic acid and 10 ml of thionyl chloride, and stirred at 8°C for an hour. Chloroform layer which was separated, was washed with 0.3% aqueous hydrochloride solution, 5% aqueous sodium bicarbonate solution, and then water. Chloroform was evaporated in reduced pressure to yield 8.7 g of crude product as oil. To purify the product, above crude product was chromatographed on silicagel using ethylacetate as developing solvent. The pure product was viscous oil and showed only one spot (Rf 0.60) on TLC (silicagel; ethylacetate, IR (liquid film) 1670 cm-1, UV λmaxMeOH 268 nm.

Workup

customChloroform layer which was separated
washwas washed with 0.3% aqueous hydrochloride solution, 5% aqueous sodium bicarbonate solution
customChloroform was evaporated in reduced pressure

Sources & evidence

ORD record: ord-d9071daa7c4c4822929cdf2ca5e2fa4b
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03935221

Linked notes

Loading…