Acetic Anhydride → HCID 21973825, compound

HRID 1265143Notes

Reaction equation

HRID 1265143 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][C:13]([CH3:16])([NH2:15])[CH3:14])[C:5]([CH3:17])=[C:4]([CH3:18])[N:3]=1.C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][C:13]([NH:15][C:26](=[O:28])[CH3:27])([CH3:14])[CH3:16])[C:5]([CH3:17])=[C:4]([CH3:18])[N:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21973832HCID 21973832, compound

Product 1

HCID 21973825HCID 21973825, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of gave N1-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)-2-methylpropane-1,2-diamine (3.14 g, 10.9 mmol) in 50 mL of CH2Cl2 was cooled to 0° C. under N2 and treated with triethylamine (2.84 mL, 20.4 mmol) and acetic anhydride (1.01 mL, 10.7 mmol). After stirring for 2 h, the reaction was quenched by the addition of saturated aqueous NaHCO3. CH2Cl2 (100 mL) was added and the organic layer was separated. The organic layer was then washed with cold H2O (2×) and brine. The organic portion was dried with Na2SO4 and concentrated to give N-{2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (2.80 g) as a yellow foam.

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous NaHCO3
  2. additionCH2Cl2 (100 mL) was added
  3. customthe organic layer was separated
  4. washThe organic layer was then washed with cold H2O (2×) and brine
  5. dry with materialThe organic portion was dried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c70c9461383444083c54708147a736b
Source dataset
uspto-grants-2003_04
Patent number
US06545016B1

Reaction notes

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