Triethylamine → 5-Chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester

HRID 1094977Notes

Reaction equation

HRID 1094977 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[Na+].[SH:31][CH2:32][CH2:33][S:34]([O-:37])(=[O:36])=[O:35].COC1C=C(C=CC=1OC)C(Cl)=O>C(Cl)Cl>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[NH:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][S:31][CH2:32][CH2:33][S:34]([OH:37])(=[O:36])=[O:35])[CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 231072215-Chloro-2-(3-chloromethyl-benzoylamino)-benzoic acid methyl esterHCID 23662354Mesna

Product 1

HCID 870861295-Chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl esterYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Subsequently, methyl 5-chloro-2-[3-(chloromethyl)benzoyl]aminobenzoate (1.8 g) was dissolved in anhydrous methylene chloride. Triethylamine (1.5 ml) and 2-mercaptoethanesulfonic acid sodium salt (compound B′) (1.3 g) were added to the solution at room temperature, and the mixture was stirred at 40° C. for 4 days. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over sodium sulfate, and was then concentrated. The residue was purified by column chromatography on silica gel to give 5-chloro-2-[3-(2-sulfo-ethylsulfanylmethyl)-benzoylamino]-benzoic acid methyl ester (1.08 go yield 46.1%) as a useful intermediate.

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f7bfe6004e574a14a2c0cafaf77ce783
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

Loading…