Water → Tert-butyl 2-[(4-methylphenyl)amino]acetate

HRID 2115327Notes

Reaction equation

HRID 2115327 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C.O>C1COCC1>[C:14]([O:13][C:11](=[O:12])[CH2:10][NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 7813p-ToluidineHCID 79177tert-Butyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 13599134Tert-butyl 2-[(4-methylphenyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-toluidine (200 mmol) in THF (500 mL) was treated with tert-butyl bromoacetate (220 mmol) and DIPEA (440 mmol) at RT. The reaction mixture was heated to reflux for 16 h and cooled to RT. Water (200 mL) and EE (500 mL) were added, the layers were separated and the aqueous layer was extracted twice with ethyl acetate (100 mL). The combined organic layers were washed with water and brine. The solvents were removed in vacuo and the residue (44 g) was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate (100 mL)
  5. washThe combined organic layers were washed with water and brine
  6. customThe solvents were removed in vacuo
  7. customthe residue (44 g) was used without further purification

Sources & evidence

ORD record
ord-2b9fadee6e15438597dece99ab34fe62
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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