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

HRID 371901Notes

Reaction equation

HRID 371901 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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3501432-Methyl-5-nitrobenzonitrileHCID 43464382-(Phenylthio)benzothiazole

Product 1

HCID 544510572-(2-Cyano-4-nitrobenzylidene)-3-ethylbenzothiazoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperatureThe reaction mixture was refluxed two hours
  2. temperaturecooled for several hours
  3. customThe green iridescent crystalline product was collected
  4. washwashed with a small amount of acetonitrile
  5. customAfter drying 1.13 g
  6. customof product, m.p. 237°-9° (dec.) was obtained

Sources & evidence

ORD record
ord-80aa2033a3f64d36ad92edc52cabcb0b
Source dataset
uspto-grants-1978_05
Patent number
US04088497

Reaction notes

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