3,3-Dimethylbutanoyl chloride → HCID 59253284, compound

HRID 643692Notes

Reaction equation

HRID 643692 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.CCN(C(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 mixture was washed with saturated sodium hydrogencarbonate aqueous solution-(100 mL×2), brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was washed with ethyl acetate to afford the title compound (11.2 g, 70%) as a white solid.

Workup

  1. washThe mixture was washed with saturated sodium hydrogencarbonate aqueous solution-(100 mL×2), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-323f389878fe4f7b9d9a14e94de155e2
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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