O-Phenylenediamine → HCID 22139864, compound

HRID 2250507Notes

Reaction equation

HRID 2250507 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-c2a8fb043c9047be92ab89241a938d1b
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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