Water → HCID 66683311, compound

HRID 1662146Notes

Reaction equation

HRID 1662146 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20][C:21](Cl)=[O:22].O>ClCCl>[Br:18][CH2:19][CH2:20][C:21]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 805742-tert-ButylanilineHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 66683311HCID 66683311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-tert-butylaniline (Aldrich, 24.7 g, 166 mmol) was dissolved in dichloromethane (100 mL) and potassium carbonate (47.0 g, 340 mmol) was added. 3-Bromopropionyl chloride (29.1 g, 170 mmol) in dichloromethane (50 mL) was added dropwise and the mixture stirred for 3 hours at ambient temperature. Water was added slowly to quench the mixture, and the organic layer was separated and washed twice with water, dried with magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (s, 9H), 2.97 (t, J=6.44 Hz, 2H), 3.74 (t, J=6.27 Hz, 2H), 7.00-7.06 (m, 1H), 7.16-7.25 (m, 2H), 7.36-7.42 (m, 1H), 9.35 (s, 1H). MS (DCI) m/z 284.0 (M+H)+.

Workup

  1. customto quench the mixture
  2. customthe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adae3c31bfcd4c6d8d5f0787abd9d696
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

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