3,3-Dimethylbutanoyl chloride → HCID 59253284, compound

HRID 643708Notes

Reaction equation

HRID 643708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:23]([CH2:27][C:28](Cl)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[C:4]([NH:13][C:28](=[O:29])[CH2:27][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 81531DiisopropylethylamineHCID 43115327HCID 43115327, compound

Product 1

HCID 59253284HCID 59253284, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N1-(cyclopropylmethyl)benzene-1,2-diamine (Step B, 11.3 g, 46.9 mmol) and N,N-diisopropylethylamine (6.06 g, 46.9 mmol) in ethyl acetate (88 mL) was added tert-butylacetyl chloride (6.31 g, 46.9 mmol) at 0° C. and the mixture was allowed to warm to room temperature for 15 h. The reaction mixture was washed with saturated sodium hydrogen carbonate aqueous solution (100 mL×2), brine (50 mL). The resulting ethyl acetate solution of reaction mixture was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was washed with ethyl acetate to afford the title compound (11.2 g, 70%) as a white solid.

Workup

  1. washThe reaction mixture was washed with saturated sodium hydrogen carbonate aqueous solution (100 mL×2), brine (50 mL)
  2. customThe resulting ethyl acetate solution of reaction mixture
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe crude product was washed with ethyl acetate

Sources & evidence

ORD record
ord-7f08a077e4354aecb32b9b6225f77b84
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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