Triethylamine → Methyl 4-chloro-3-[(4-chloro-1-oxobutyl)amino]benzoate

HRID 852536Notes

Reaction equation

HRID 852536 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:8][O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([NH2:18])[CH:12]=1.CCN(CC)CC>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([NH:18][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 593055Methyl 3-Amino-4-chlorobenzoate

Product 1

HCID 63309021Methyl 4-chloro-3-[(4-chloro-1-oxobutyl)amino]benzoateYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chlorobutyryl chloride (2.82 g, 20 mmol, 2.0 equiv) in CH2Cl2 (5 ml) was added over 2 min to a stirred solution of 3-amino-4-chloro-benzoic acid methyl ester (D27c) (1.66 g, 10 mmol, 1 equiv) and NEt3 (2.22 g, 22 mmol, 2.2 equiv) in CH2Cl2 (40 ml). The resulting mixture was stirred for 1 h at room temperature then washed with 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with CH2Cl2 to give 4-chloro-3-(4-chloro-butanoylamino)-benzoic acid methyl ester (D28c) (1.81 g, 48%) as a pale pink solid.

Workup

  1. washthen washed with 2N aqueous HCl solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-339f1110312847cdba5038a8ccfe76b3
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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