Acetyl chloride → HCID 86697212, compound

HRID 237548Notes

Reaction equation

HRID 237548 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][NH2:11])=[CH:4][C:3]=1[CH3:12].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][NH:11][C:20](=[O:22])[CH3:21])=[CH:4][C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 84792074HCID 84792074, compound

Product 1

HCID 86697212HCID 86697212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-(4-bromo-3,5-dimethylphenyl)ethanamine (100 mg) and triethylamine (68 μL) in dichloromethane (3 mL) is added acetyl chloride (31 μL). The mixture is stirred for 2 hours at 0° C. Then the mixture is partitioned between dichloromethane and water. The organic phase is separated and dried (MgSO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 25 mg; LC (method 7): tR=0.98 min; Mass spectrum (ESI+): m/z=270 [M+H]+.

Workup

  1. customThen the mixture is partitioned between dichloromethane and water
  2. customThe organic phase is separated
  3. dry with materialdried (MgSO4)
  4. customThe solvent is evaporated
  5. customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-afc9a0d1d6d44201bd5970893bb5ef2e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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