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

HRID 1244801Notes

Reaction equation

HRID 1244801 reaction equation
N1C2C(=CC(O[CH:12]([CH2:22][CH3:23])[C:13]([NH:15][C:16]([CH3:21])([CH3:20])[C:17]#[C:18][CH3:19])=[O:14])=CC=2)C=CC=1.[Br:24]C(CC)C(Br)=O.C(N(CC)CC)C.O>ClCCl>[Br:24][CH:12]([CH2:22][CH3:23])[C:13]([NH:15][C:16]([CH3:21])([CH3:20])[C:17]#[C:18][CH3:19])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1172932-Bromobutanoyl bromideHCID 692539492-(6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3 °C

Procedure

The product from Step 3 (5.0 g) was dissolved in dry dichloromethane (200 ml), cooled to 3° C. with stirring then 2-bromobutyryl bromide (6.25 g) was added followed by dropwise addition of dry triethylamine (10.93 ml), maintaining the reaction at 5° C. The suspension, which had formed during the reaction, was stirred at ambient temperature for 1 hour then 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, m.p. 79–81° C.

Workup

  1. temperaturemaintaining
  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-e9db5b7cf1ca45e6a3f76a955b2f39cd
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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