Iodoethane → 6-nitro-3-ethyl-2(3H)-benzothiazolone
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=C1CCC[CH2:16][CH2:15]2.ICC>CN(C)C=O.O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:15][CH3:16])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]Participants
6
Procedure
A solution of 6-nitro-2-benzothiazolinone (2.5 g, 12.7 mmol) in anhydrous N,N-dimethylformamide (25 mL) under N2 is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.48 mL, 16.6 mmol) dropwise followed by iodoethane (1.22 mL, 15.3 mmol). Following a slight exotherm, the reaction mixture is stirred at ambient temperature for 21 h, diluted with water (20 mL) and filtered to give the title compound, mp 200–203° C.
Workup
- filtrationfiltered
Sources & evidence
- ORD record
- ord-c6ebdcfd75854a4f878500e553a815c5
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141588B2
Reaction notes
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