Diisopropylethylamine → 2-(2-Cyano-4-nitrobenzylidene)-3-ethylbenzothiazoline

Reaction equation

C1(S[C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)C=CC=CC=1.[C:17]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[CH3:28])#[N:18].[CH:29](N(C(C)C)CC)(C)[CH3:30]>C(#N)C>[C:17]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[CH:28]=[C:8]1[N:12]([CH2:29][CH3:30])[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[S:9]1)#[N:18]

Participants

Procedure

2-Phenylthiobenzothiazole ethiodide (3.99 g., 0.01 mole) and 2.00 g. (0.012 mole) of 2-cyano-4-nitrotoluene were dissolved in 25 ml. of acetonitrile and then 2.58 g. (0.02 mole) of diisopropyl ethylamine was added. The reaction mixture was refluxed two hours and then cooled for several hours. The green iridescent crystalline product was collected and washed with a small amount of acetonitrile. After drying 1.13 g. of product, m.p. 237°-9° (dec.) was obtained.