Water → Methyl 3-chloro-4-(5-chloro-pentanoyl-amino)-benzoate

HRID 551188Notes

Reaction equation

HRID 551188 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[Cl:20].O>C1COCC1>[Cl:20][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:10]=1[NH:9][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 740895-Chlorovaleryl chlorideHCID 1515284Methyl 4-Amino-3-chlorobenzoate

Product 1

HCID 69205032Methyl 3-chloro-4-(5-chloro-pentanoyl-amino)-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 696 μl (0.84 g, 5.39 mmol) 5-chloro-pentanoylchloride in 10 ml THF is slowly added dropwise to 1.00 g (5.39 mmol) methyl 4-amino-3-chloro-benzoate in 20 ml THF with 1 ml TEA with stirring in the ice bath. After stirring for 16 hours at ambient temperature, for 3 hours at 50° C. and for 3 hours at reflux temperature the mixture is poured into water and extracted with ethyl acetate. After the organic phases have been dried over sodium sulphate the mixture is evaporated down i. vac. and the residue remaining is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 85:15).

Workup

  1. temperatureat reflux temperature the mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter the organic phases have been dried over sodium sulphate the mixture
  4. customis evaporated down i
  5. customand the residue remaining is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 85:15)

Sources & evidence

ORD record
ord-270d7dd76989493b96239d0e02765453
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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