Benzo(d)thiazol-2-amine → 5-(Imidazo[2,1-b]benzothiazol-2-yl)-3-nitropyrocatechol

HRID 274471

Reaction equation

HRID 274471 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([OH:15])[CH:6]=1)=O.[NH2:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>C(O)C>[N:16]1[C:3]([C:5]2[CH:6]=[C:7]([OH:15])[C:8]([OH:14])=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=2)=[CH:2][N:21]2[C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18][C:17]=12

Participants

4

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 218455962-Bromo-1-(3,4-dihydroxy-5-nitro-phenyl)-ethanone

Product 1

HCID 214590695-(Imidazo[2,1-b]benzothiazol-2-yl)-3-nitropyrocatechol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.95 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone, 1.06 g of 2-aminobenzothiazole and 50 ml of ethanol is heated to boiling under reflux for 17 hours. The reaction mixture is then cooled to room temperature, whereupon the crystals are removed by filtration under suction. There is obtained 5-(imidazo[2,1-b]benzothiazol-2-yl)-3-nitropyrocatechol of m.p. 303°-305° (from N,N-dimethylformamide/methanol).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 17 hours
  3. customare removed by filtration under suction

Sources & evidence

ORD record
ord-c6b1a535c5ee4613b184f2f0f99a485a
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Linked notes

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