O-Phenylenediamine → HCID 22139864, compound

HRID 1825917Notes

Reaction equation

HRID 1825917 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[Cl:9][C:10]1[C:11]([N:15]=[C:16]=[S:17])=[CH:12][S:13][CH:14]=1>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:16]([NH:15][C:11]1[C:10]([Cl:9])=[CH:14][S:13][CH:12]=1)=[S:17]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 22139828HCID 22139828, compound

Product 1

HCID 22139864HCID 22139864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.86 g of 1,2-diaminobenzene (o-phenylenediamine) is added to a solution of 1.4 g of 4-chloro-3-thienyl isothiocyanate in 40 ml of anhydrous THF, the mixture is stirred at room temperature for about 20 hours and the solvent is distilled off under reduced pressure. The residue is treated with water and extracted with ethyl acetate, the solvent is distilled off again and the residue is purified using medium-pressure silica gel column chromatography using a 1:1 mixture of ethyl acetate and toluene. Brown-yellow solid.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. additionThe residue is treated with water
  3. extractionextracted with ethyl acetate
  4. distillationthe solvent is distilled off again
  5. customthe residue is purified
  6. additiona 1:1 mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-c76248537d2e4cf2aad7baaa95255734
Source dataset
uspto-grants-2006_05
Patent number
US07049333B2

Reaction notes

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