HCID 12036785, compound → HCID 15375068, compound

HRID 450084Notes

Reaction equation

HRID 450084 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC(N(C2C=CC([N+]([O-])=O)=CC=2)C2SC=CN=2)=CC=1)([O-])=O>C(O)(=O)C.[Zn]>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[NH:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 12036785HCID 12036785, compoundHCID 86621148HCID 86621148, compound

Product 1

HCID 15375068HCID 15375068, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
67.5 °C

Procedure

Zinc powder (1.2 g, 18.46 mmol) was added to a solution of 400 mg of a mixture of (4-nitro-phenyl)-thiazol-2-yl-amine and bis-(4-nitrophenyl)-thiazol-2-yl amine in acetic acid (8 ml) and then heated at 65-70° C. for 2 hr. The reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate. The organic layer was washed with dilute sodium hydroxide solution, then water, brine and dried. Evaporation yielded a crude mixture which was chromatographed over silica gel using 1% methanol in chloroform to give N-thiazol-2-yl-benzene-1,4-diamine (75 mg, 21.7%), as a solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with dilute sodium hydroxide solution
  4. dry with materialwater, brine and dried
  5. customEvaporation
  6. customyielded a crude mixture which
  7. customwas chromatographed over silica gel using 1% methanol in chloroform

Sources & evidence

ORD record
ord-3f2d2cfba944448a99f908ec0e4a5780
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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