Triethylamine → N-(2-{[(2-chloroethyl)sulfonyl]amino}ethyl)-2-nitrobenzenesulfonamide

HRID 550795Notes

Reaction equation

HRID 550795 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][NH2:16])(=[O:12])=[O:11])([O-:3])=[O:2].[Cl:17][CH2:18][CH2:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[Cl:17][CH2:18][CH2:19][S:20]([NH:16][CH2:15][CH2:14][NH:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 11471557N-(2-Aminoethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 67197523N-(2-{[(2-chloroethyl)sulfonyl]amino}ethyl)-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-(2-nitrobenzenesulfonyl)ethylenediamine, 2-chloroethanesulfonyl chloride, triethylamine, and methylene chloride was stirred at 0° C. for 3 hours to yield N-(2-{[(2-chloroethyl)sulfonyl]amino}ethyl)-2-nitrobenzenesulfonamide. This compound was dissolved in acetonitrile, here were added cesium carbonate and tetrabutylammonium iodide, and the mixture was stirred at 80° C. for 21 hours to yield 5-[(2-nitrophenyl)sulfonyl]-1,2,5-thiadiazepane 1,1-dioxide. This compound was dissolved in acetonitrile, here were added 4-methylbenzenethiol and potassium carbonate, and the mixture was stirred at 50° C. for 21 hours to yield 1,2,5-thiadiazepane 1,1-dioxide.

Sources & evidence

ORD record
ord-e47c8bcc378b4b50ba307d9356a610e3
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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