Dimethylformamide → 3-(3-chloropropyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237466Notes

Reaction equation

[O:1]=[S:2]1(=[O:16])[N:7]([CH2:8][CH2:9][CH2:10]O)[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[NH:3]1.S(Cl)([Cl:19])=O.CN(C)C=O>ClCCl>[Cl:19][CH2:10][CH2:9][CH2:8][N:7]1[CH2:6][C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[NH:3][S:2]1(=[O:16])=[O:1]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-(2,2-dioxido-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)propan-1-ol (1.0 g, 4.1 mmol) in dichloromethane (20 mL) was treated with thionyl chloride (0.91 mL, 12.3 mmol) and dimethylformamide (0.20 mL) and stirred at 23° C. for 16 hours. Additional thionyl chloride (0.30 mL, 4.1 mmol) was added and stirring was continued for an additional 4 hours. The reaction mixture was quenched by the addition of methanol (5 mL) and evaporated. Flash chromatography (SiO2, 3-40% ethyl acetate/hexanes) provided 3-(3-chloropropyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.85 g, 79%) as a yellow oil:

Workup

stirringstirring
waitwas continued for an additional 4 hours
customThe reaction mixture was quenched by the addition of methanol (5 mL)
customevaporated

Sources & evidence

ORD record: ord-a9e0144017d04716a14cae8a64026f32
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718652B2

Reaction notes

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