Water → Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

HRID 2094310Notes

Reaction equation

HRID 2094310 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26](Cl)=[O:27].O>C1COCC1>[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2736799Methyl 4-amino-3-methylbenzoateHCID 860693723-(2-Chloroethoxy)propanoyl chloride

Product 1

HCID 67048278Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.70 g (10.3 mmol) methyl 4-amino-3-methyl-benzoate in 10 ml THF are combined with 2.84 ml (20.6 mmol) triethylamine and stirred for 20 minutes at ambient temperature. Then a solution of 1.78 g (10.4 mmol) 3-(2-chloro-ethoxy)-propionic acid-chloride in 25 ml THF is added dropwise and the mixture is stirred for a further 2.5 hours at ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3->6:4).

Workup

  1. stirringthe mixture is stirred for a further 2.5 hours at ambient temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customevaporated down completely
  5. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3->6:4)

Sources & evidence

ORD record
ord-a0a2b69fc37849aab83acc7c7a2c14f2
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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