Water → HCID 4100598, compound

HRID 859119Notes

Reaction equation

HRID 859119 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].C(N(CC)CC)C.O>O1CCOCC1>[CH3:8][O:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 4100598HCID 4100598, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Pivaloyl chloride (120 g, 1 mol) was added dropwise at ambient temperature to a stirred solution of 2-methoxyaniline (123 g, 1 mol) and triethylamine (111 g, 1.1 mol) in 1,4-dioxane (1200 ml), the mixture was stirred at ambient temperature for 2 hours, then it was poured into water (3000 ml). The product was extracted into ethyl acetate (3×300 ml), then the combined extracts were dried (MgSO4) and the solvents were removed in vacuo to give N-(2-methoxyphenyl)pivalamide (198 g; 96%) as a low-melting solid which was used without further purification.

Workup

  1. extractionThe product was extracted into ethyl acetate (3×300 ml)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-1a2a77d01d574b699a439e11e0a70846
Source dataset
uspto-grants-2006_12
Patent number
US07151102B2

Reaction notes

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