2-Thiophenecarboxylic acid → 5-Nitro-2-(thiophen-2-yl)-1,3-benzothiazole

HRID 1287836Notes

Reaction equation

HRID 1287836 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:11].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=O>C(Cl)(Cl)Cl>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[S:11][C:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)=[N:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 107002-Thiophenecarboxylic acidHCID 63364002-Amino-4-nitrobenzenethiol

Product 1

HCID 127819405-Nitro-2-(thiophen-2-yl)-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Amino-4-nitrobenzenethiol, 9.6 g (0.054 mole) and thiophene-2-carboxylic acid, 10.0 g (0.075 mole) are added to a solution of 54 g of PPE in 130 cc CHCl3. The mixture is heated at reflux for 2 hours. It is then concentrated in vacuo and the residue poured over ice. The pH is adjusted to 10 with 50% NaOH solution, and the precipitate filtered and washed with H2O. Drying in vacuo yields 15 g of the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. concentrationIt is then concentrated in vacuo
  4. additionthe residue poured over ice
  5. filtrationthe precipitate filtered
  6. washwashed with H2O
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-dee99fe4813e4debbc6f008378d97654
Source dataset
uspto-grants-1976_10
Patent number
US03985885

Reaction notes

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