Isobutylamine → 2-Chloro-N-isobutylacetamide

HRID 1590408Notes

Reaction equation

HRID 1590408 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]([NH2:10])[CH:7]([CH3:9])[CH3:8]>CCOCC>[CH2:6]([NH:10][C:3](=[O:4])[CH2:2][Cl:1])[CH:7]([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 6577Chloroacetyl chloride

Product 1

HCID 2223592-Chloro-N-isobutylacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloroacetyl chloride (ex. Aldrich) (50 g) was added dropwise, with stirring to isobutylamine (ex. Aldrich) (70 ml) in dry ether (250 ml) at 0° C. When the mixture had reached room temperature it was worked up in conventional fashion to give N-isobutyl 2-chloroacetamide. The latter (20 g) was heated for 3 hours at 120° C. with triethylphosphite (23 g). The mixture was subjected to distillation in vacuo to give N-isobutyl diethylphosphono acetamide (22.5 g, bp. 140-142.5° C. at 0.1 mm).

Workup

  1. customhad reached room temperature

Sources & evidence

ORD record
ord-bf99e01407ae41138ca2079bb93fde26
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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