Isopropyl iodide → 6-nitro-3-isopropyl-2(3H)-benzothiazolone

HRID 896124Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].N12CCCN=C1CC[CH2:17][CH2:16][CH2:15]2.IC(C)C>CN(C)C=O.O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH:16]([CH3:17])[CH3:15])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred solution of 6-nitro-2-benzothiazolinone (5.0 g, 25.5 mmol) in anhydrous N,N-dimethylformamide (51 mL) under N2 is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (4.96 mL, 33.1 mmol) dropwise. Following a slight exotherm, the reaction mixture is heated up to 50° C. and treated with 2-iodopropane (12.7 mL, 127 mmol). The resulting mixture is quickly heated up to 75° C., stirred at this temperature for 40 mins, cooled to ambient temperature and diluted with ice (100 mL) and water (100 mL). The precipitate is isolated by filtration and recrystallized from ethyl acetate/hexanes to give the title compound, mp 138-142° C.

Workup

temperatureThe resulting mixture is quickly heated up to 75° C.
temperaturecooled to ambient temperature
customThe precipitate is isolated by filtration
customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-60dfaa3b7716471bb5b52ba7501987ed
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919329B2

Reaction notes

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