4-Iodo-3-aminothioanisole → 4-Methylsulfanyl-2'-amino-biphenyl-2-ylamine

HRID 751022Notes

Reaction equation

HRID 751022 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[C:5]([NH2:18])[CH:4]=1.IC1C=CC(SC)=CC=1N>O=[Pt]=O.C(O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[C:5]([NH2:18])[CH:4]=1

Participants

5

Reactant 2

HCID 597545314-Iodo-3-aminothioanisoleHCID 674031774-Methylsulfanyl-2'-nitro-biphenyl-2-ylamine

Product 1

HCID 674031524-Methylsulfanyl-2'-amino-biphenyl-2-ylamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A flask was charged with ca. 1 mmol of 4-Methylsulfanyl-2′-nitro-biphenyl-2-ylamine, 15 mL of ethanol, and 0.1 mmol of PtO2, and stirred under hydrogen atmosphere at 40 psi for 10 minutes. The reaction mixture was filtered through diatomaceous earth, washed with ethanol, and the combined organic layer was evaporated to dryness. The crude material was purified by preparative HPLC. The same material can also be prepared by the previous method, (Suzuki coupling conditions) starting from 4-iodo-3-aminothioanisole, and purified by preparative HPLC.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashed with ethanol
  3. customthe combined organic layer was evaporated to dryness
  4. customThe crude material was purified by preparative HPLC
  5. customThe same material can also be prepared by the previous method, (Suzuki coupling conditions)
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cbb4e91f03ef419aacfae46c265e3f5f
Source dataset
uspto-grants-2008_07
Patent number
US07405235B2

Reaction notes

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