5-Chloro-benzothiazole-2-sulfonyl chloride → [2-(5-Chloro-benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester

HRID 1064608Notes

Reaction equation

HRID 1064608 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[N:19][C:18]=2[CH:26]=1>>[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][S:22]([C:20]1[S:21][C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:26][C:18]=2[N:19]=1)(=[O:24])=[O:23])[CH3:4]

Participants

3

Reactant 2

HCID 218684555-Chloro-benzothiazole-2-sulfonyl chlorideHCID 74889816N-beta-Aminoethyl-gly-oet 2hcl

Product 1

HCID 21868385[2-(5-Chloro-benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl esterYield 87%

Procedure

The title compound (657 mg, 87%) was synthesized by the reaction of N-(2-aminoethyl)-glycine ethyl ester 2HCl (398 mg, 2.0 mmol) with 5-chloro-benzothiazole-2-sulfonyl chloride (536 mg, 2.0 mmol) as per the procedure of example 1. 1H NMR (500 MHz; DMSO-d6) δ 8.32 (d, 1H), 8.31 (s, 1H), 7.71 (d, 1H), 4.02 (q, 2H), 3.25 (s, 2H), 3.14 (t, 2H), 2.62 (t, 2H), 1.15 (t, 3H).

Sources & evidence

ORD record
ord-903e703f22644c05aca870689a4503f8
Source dataset
uspto-grants-2005_11
Patent number
US06969766B2

Reaction notes

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