Hydrochlorothiazide → 2-(2-Bromoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

HRID 868205

Reaction equation

[Cl:1][C:2]1[C:3]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:4][C:5]2[S:10](=[O:12])(=[O:11])[NH:9][CH2:8][NH:7][C:6]=2[CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:24][CH2:25][CH2:26]Br.C(C(Br)C([O-])=O)C1C=CC=CC=1>>[Br:24][CH2:25][CH2:26][N:9]1[CH2:8][NH:7][C:6]2[CH:13]=[C:2]([Cl:1])[C:3]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:4][C:5]=2[S:10]1(=[O:12])=[O:11]

Participants

Reactant 4

HCID 3639Hydrochlorothiazide

HCID 78391,2-Dibromoethane

HCID 10796Cesium carbonate

HCID 21881508Benzylbromoacetate

Product 1

HCID 142809712-(2-Bromoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

Procedure

Treat 6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine with Cs2CO3 and substitute 1,2-dibromoethane for benzylbromoacetate in the procedure of Example 7, step A to obtain 2-(2-bromoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine.

Sources & evidence

ORD record: ord-6b9669262562417cac6d976e2a44bae5
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04778795

Linked notes

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