Water → 66003-33-6

HRID 1608691Notes

Reaction equation

HRID 1608691 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.O>C(OCC)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 459251866003-33-6

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 35 g 4-chlorobutyrylchloride in 100 ml of diethylether is added dropwise to a stirred solution of 19 g tert-butylamine and 28 g triethylamine in 400 ml of diethylether. After reflux for one hour the mixture is poured into water, the organic phase is separated and the water layer is extracted with diethylether. The combined organic phase is successively washed with water and saturated NaCl solution, and then dried. After evaporating the solvent, 4-chloro-N-tert-butylbutyric amide is obtained in a yield of 40.8 g. The product can be purified by recrystallization from methanol: m.p. 62.5°-64° C.

Workup

  1. temperatureAfter reflux for one hour the mixture
  2. customthe organic phase is separated
  3. extractionthe water layer is extracted with diethylether
  4. washThe combined organic phase is successively washed with water and saturated NaCl solution
  5. customdried
  6. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-7618369a96f44a0086fd526a073a7397
Source dataset
uspto-grants-1995_03
Patent number
US05395946

Reaction notes

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