Water → 2-bromo-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374903Notes

Reaction equation

HRID 1374903 reaction equation
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[C:4]#[C:5][CH3:6].[Br:9][CH:10]([CH2:14][CH3:15])[C:11](Br)=[O:12].C(N(CC)CC)C.O>ClCCl>[Br:9][CH:10]([CH2:14][CH3:15])[C:11]([NH:2][C:3]([CH3:8])([CH3:7])[C:4]#[C:5][CH3:6])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1172932-Bromobutanoyl bromideHCID 219231292-Methylpent-3-yn-2-amine hydrochloride

Product 1

HCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3 °C

Procedure

4-Amino-4-methylpent-2-yne hydrochloride (5.0 g) was dissolved in dry dichloromethane (200 ml) and cooled to 3° C. with stirring. 2-Bromobutyryl bromide (6.25 g) was added followed by the dropwise addition of dry triethylamine (10.93 ml) whilst maintaining the reaction at 5° C. The suspension, which had formed during the reaction, was stirred at ambient temperature for 1 hour and water was added. The organic phase was separated, washed with water, dried over magnesium sulphate then evaporated under reduced pressure. The residue was fractionated by chromatography (silica; hexane/diethyl ether, 3:1 by volume) to give the required product, 5.2 g, as a colourless solid, mp 79–81° C.

Workup

  1. temperaturewhilst maintaining
  2. customthe reaction at 5° C
  3. customThe suspension, which had formed during the reaction
  4. stirringwas stirred at ambient temperature for 1 hour
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-44c94ed8beba42a5bf67834467066ae8
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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