4-Toluenesulfonyl chloride → Methyl 4-(2-p-toluenesulphonamido-indan-5-yl)-4-oxobutyrate

HRID 620198Notes

Reaction equation

HRID 620198 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:9]=2)[CH2:4]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:9]=3)[CH2:4]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23050575Methyl 4-(2-amino-indan-5-yl)-4-oxobutyrate hydrochloride

Product 1

HCID 14071511Methyl 4-(2-p-toluenesulphonamido-indan-5-yl)-4-oxobutyrate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.0 g (21.1 mmol) of methyl 4-(2-amino-indan-5-yl)-4-oxobutyrate hydrochloride are suspended in 60 ml of chloroform and 5.0 g (25.3 mmol) of p-toluenesulphonyl chloride are added. 5.1 g (50 mmol) of triethylamine are added, with vigorous stirring, a clear solution being formed. After 20 hours at room temperature, the mixture is washed with water, the chloroform solution is evaporated and the residue is recrystallised from methanol.

Workup

  1. customa clear solution being formed
  2. washthe mixture is washed with water
  3. customthe chloroform solution is evaporated
  4. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-108a7eafbf084c76b4f02daf629fd8bc
Source dataset
uspto-grants-1989_04
Patent number
US04820705

Reaction notes

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