Diisopropylethylamine → HCID 44203076, compound

HRID 77369Notes

Reaction equation

HRID 77369 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]([CH3:8])[CH3:7])=[O:4].C(N(CC)C(C)C)(C)C.[F:18][C:19]1[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>ClCCl>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=1)[C:24]([NH:1][CH2:2][C:3]([NH:5][CH:6]([CH3:8])[CH3:7])=[O:4])=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5338492-Amino-N-isopropylacetamideHCID 156548685-Fluoro-2-nitrobenzoyl chloride

Product 1

HCID 44203076HCID 44203076, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-N-isopropylacetamide (11.3 g, 97.0 mmol) and N,N-diisopropylethylamine (20.1 g, 162 mmol) in dichloromethane (200 mL) was cooled using an ice water bath. A solution of 5-fluoro-2-nitrobenzoyl chloride (16.5 g, 81.0 mmol) in dichloromethane (200 mL) was added dropwise over 15 minutes. The resulting solution was stirred overnight. The reaction mixture was washed with 2N HCl solution (2×250 mL), brine (250 mL) and then dried over magnesium sulphate. The solution was filtered before concentrating under reduced pressure to afford 5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (18.5 g, 65.0 mmol).

Workup

  1. washThe reaction mixture was washed with 2N HCl solution (2×250 mL), brine (250 mL)
  2. dry with materialdried over magnesium sulphate
  3. filtrationThe solution was filtered
  4. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-e36acb5a9442418b8149bd6620d8e734
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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