Tributylamine → 1-Butanamine, N,N-dibutyl-, hydrochloride (1:1)

HRID 2199366

Reaction equation

HRID 2199366 reaction equation
P(Cl)(Cl)([Cl:3])=S.C(N)CCC.[CH2:11]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>C(OCC)(=O)C>[ClH:3].[CH2:20]([N:15]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:21][CH2:22][CH3:23]

Participants

5

Procedure

To this end, thiophosphoryl chloride and a primary alkylamine, for example n-butylamine, are reacted in molar ratios of preferably 0.9 to 1.1 mol of amine per mole of thiophosphoryl chloride in an inert solvent, for example ethyl acetate. The auxiliary base used is a trialkylamine, for example tri-n-butylamine, which is reacted to give the tri-n-butylamine hydrochloride. In a second reaction step, the N-alkylthiophosphoryl dichloride which has been formed in the first reaction is reacted with ammonia at temperatures of between preferably −20° C. and 50° C. to give the desired product N-alkylthiophosphoric triamide. In parallel with, and independently of, the second reaction step, ammonia acts as base 2 and accepts the hydrogen chloride from the trialkylamine hydrochloride with formation of ammonium chloride.

Sources & evidence

ORD record
ord-8c1ccd5fe3ab4d7b80831e24ad302a51
Source dataset
uspto-grants-2016_06
Patent number
US09359269B2

Linked notes

Loading…