Sodium borohydride → 7-chloro-4-cyclopropylmethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 17846Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH2:12][CH:13]3[CH2:15][CH2:14]3)[CH:7]=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[BH4-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:7][NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7-chloro-4-cyclopropylmethyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (0.7 g) in isopropanol (50 mL) there is added sodium borohydride (0.2 g) and the mixture is heated at 50° C. for 5 minutes. The reaction mixture is evaporated under reduced pressure and the residue is taken up in water (30 mL). The pH of the medium is adjusted to 5-6 by addition of 6N hydrochloric acid and the suspension is extracted three times with chloroform (30 mL). The organic phases are collected, dried over anhydrous MgSO4 and filtered. The filtrate is evaporated under reduced pressure and the residue is taken up in methanol (5 mL). Water (50 mL) is added to the methanolic solution and the precipitate which appears is collected by filtration, washed with water and dried.

Workup

customThe reaction mixture is evaporated under reduced pressure
additionThe pH of the medium is adjusted to 5-6 by addition of 6N hydrochloric acid
extractionthe suspension is extracted three times with chloroform (30 mL)
customThe organic phases are collected
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe filtrate is evaporated under reduced pressure
additionWater (50 mL) is added to the methanolic solution
filtrationthe precipitate which appears is collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-a01501c88bd247b59f02614af6653c59
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741320B2

Reaction notes

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