Hydrochloric Acid → N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide

HRID 33377Notes

Reaction equation

HRID 33377 reaction equation
[Br:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:10]([OH:26])=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1.C(OCC)(=O)C.Cl>N1C=CC=CC=1>[C:23]([C:11]1[C:10]([OH:26])=[C:9]([NH:8][C:3](=[O:4])[C:2]([Br:1])([CH3:7])[CH3:6])[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 111060492-Bromo-2-methylpropanoyl chlorideHCID 210728221-(3-Amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone

Product 1

HCID 21072865N-(3-acetyl-5-benzyloxy-2-hydroxyphenyl)-2-bromo-2-methylpropionamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.64 g (25 mmol) 2-bromo-2-methyl-propionyl chloride are added dropwise at 5 to 20° C. to a solution of 5.15 g (20 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone in 20 mL pyridine. After the addition has ended the mixture is stirred for 15 minutes, combined with ice water and 100 mL ethyl acetate and acidified with conc. hydrochloric acid. The organic phase is separated off, washed with water and dried with sodium sulphate. After the solvent has been distilled off the residue is crystallised from a diethyl ether/petroleum ether mixture.

Workup

  1. additionAfter the addition
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried with sodium sulphate
  5. distillationAfter the solvent has been distilled off the residue
  6. customis crystallised from a diethyl ether/petroleum ether mixture

Sources & evidence

ORD record
ord-2050f9e6eaf04ed689d426045a19745f
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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