Methyl iodide → 1-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

HRID 840194Notes

Reaction equation

C([O-])(O)=O.[Na+].[N+:6]([C:9]1[CH:10]=[CH:11][C:12]2[NH:16][S:15](=[O:18])(=[O:17])[CH2:14][C:13]=2[CH:19]=1)([O-:8])=[O:7].I[CH3:21]>O>[CH3:21][N:16]1[C:12]2[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:19][C:13]=2[CH2:14][S:15]1(=[O:18])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

NaHCO3 (0.2 g, 2.4 mmol) is dissolved in H2O (3 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (0.41 g, 1.9 mmol) is added with stirring. The mixture is heated to 80° C. for 0.5 hrs and a yellow solid formed. The mixture is cooled to 0° C. and filtered. The solid is washed with cold H2O (5 mL) then with cold EtOH (15 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (3.5 mL). Iodomethane (0.15 mL, 2.1 mmol) is added and the solution heated to 100° C. for 2 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (0.27 g, 62%) after recrystallization from EtOH. Mp 214-6° C. HRMS (FAB) calcd for C8H8N2O4S +H1 229.0283, found 229.0280.

Workup

customa yellow solid formed
temperatureThe mixture is cooled to 0° C.
filtrationfiltered
washThe solid is washed with cold H2O (5 mL)
customThe yellow solid thus obtained
customis dried under high vacuum
dissolutionthen dissolved in dry DMF (3.5 mL)
temperaturethe solution heated to 100° C. for 2 hrs
temperatureThe solution is cooled to room temperature
filtrationThe solid is collected by filtration

Sources & evidence

ORD record: ord-9f89e859229c448b86f79fe7eeaff69b
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365612B2

Reaction notes

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