Hydrochloric Acid → HCID 66756652, compound

HRID 660474Notes

Reaction equation

HRID 660474 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][C:22](=[O:25])[CH2:23]Br)([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[C:17]([O:21][C:22](=[O:25])[CH2:23][NH:16][C:10]1[CH:11]=[CH:12][C:13]([I:15])=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 66756754HCID 66756754, compound

Product 1

HCID 66756652HCID 66756652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-benzyloxy-4-iodophenylamine (2.35 g, 7.23 mmol) in DMF (15 mL) is added bromoacetic acid tert-butyl ester (1.76 g, 9.04 mmol) and K2CO3 (5.0 g, 36.2 mmol) and the mixture is heated at 50° C. for 4 h. 2N HCl solution (200 mL) is added with cooling and it is then extracted with EtOAc. The organic layer is then washed with brine, dried and concentrated. The residue is then purified by column chromatography to give the title compound as a white solid.

Workup

  1. temperaturewith cooling
  2. extractionit is then extracted with EtOAc
  3. washThe organic layer is then washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is then purified by column chromatography

Sources & evidence

ORD record
ord-797455e6ad7c495cab461352d1cef8e2
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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