Butylamine → N-Butylmethacrylamide

HRID 1982515Notes

Reaction equation

HRID 1982515 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[C:6](Cl)(=[O:10])[C:7]([CH3:9])=[CH2:8]>C1COCC1>[CH2:1]([NH:5][C:6](=[O:10])[C:7]([CH3:9])=[CH2:8])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 13528Methacryloyl chloride

Product 1

HCID 9855497N-Butylmethacrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

In a 1 liter 3-necked flask were combined 400 ml dry THF and 40 ml distilled n-butylamine (0.405 mol). After cooling to 5° C. in an ice bath, 20 ml (0.205 mol) methacryloyl chloride was added slowly so as to keep the temperature below 10° C. The precipitate was removed by filtration, and the filtrate concentrated on a rotary evaporator. 1 g DNPD was added and the oil distilled at 76°-78° C. and 20 m torr. Yield 24.3 g (84%).

Workup

  1. customIn a 1 liter 3-necked flask were combined
  2. customthe temperature below 10° C
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate concentrated on a rotary evaporator
  5. addition1 g DNPD was added
  6. distillationthe oil distilled at 76°-78° C.

Sources & evidence

ORD record
ord-ed2f99d572ba441ea7927338c4b4af02
Source dataset
uspto-grants-1986_06
Patent number
US04596858

Reaction notes

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