1,1'-Carbonyldiimidazole → 2H-1,2,4-Benzothiadiazin-3(4H)-one, 2-cyclopropyl-, 1,1-dioxide

HRID 1835835Notes

Reaction equation

HRID 1835835 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH:12]1[CH2:14][CH2:13]1)(=[O:10])=[O:9].C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C(Cl)Cl>[CH:12]1([N:11]2[C:20](=[O:21])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8]2(=[O:10])=[O:9])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 167933782-Amino-N-cyclopropylbenzenesulfonamide

Product 1

HCID 235170702H-1,2,4-Benzothiadiazin-3(4H)-one, 2-cyclopropyl-, 1,1-dioxideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of of 2-amino-N-cyclopropyl-benzenesulfonamide (6.9 g, 32.5 mmol) in CH2Cl2 (50 ml) was treated with CDI (6.5 g, 40 mmol) and stirred for 12 h at reflux. The solution was a washed with HCl (1N), dried over MgSO4 and concentrated to give 6.5 g (84%) of 2-cyclopropyl-1,1-dioxo-1,4-dihydro-2H-1λ6-benzo[1,2,4]thiadiazin-3-one as a brown solid.

Workup

  1. temperatureat reflux
  2. washa washed with HCl (1N)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8235486cb21b4df6b80a091728ab522c
Source dataset
uspto-grants-2004_08
Patent number
US06774134B2

Reaction notes

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