Water → HCID 68707090, compound

HRID 1820120Notes

Reaction equation

HRID 1820120 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH2:11])=[C:4]([CH3:12])[CH:3]=1.[C:13]([CH2:17][C:18](Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14].O>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][C:18](=[O:19])[CH2:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 815143,3-Dimethylbutanoyl chlorideHCID 5226794-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 68707090HCID 68707090, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

4-Bromo-2-methyl-6-nitro-phenylamine (2.22 g) and tert-butylacetyl chloride (1.30 g) were mixed in acetonitrile (3 mL) and heated to 140° C. for 40 minutes in a sealed microwave process vial. Water (5 mL) was added and the product was collected by filtration and washed with water and heptane to furnish 2.80 g (86% yield) of the title compound as a yellow solid. LC-MS (m/z) 329 (MH+); tR=3.07, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.01 (s, 9H), 2.21 (s, 2H), 2.29 (s, 3H), 7.87 (d, 1H), 7.95 (d, 1H), 9.77 (s, 1H).

Workup

  1. filtrationthe product was collected by filtration
  2. washwashed with water and heptane

Sources & evidence

ORD record
ord-69dbfedd2e0648d88b9e2e1df8d04b41
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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