Acetic Acid → 5-methoxy-N1-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)benzene-1,2-diamine

HRID 1848173Notes

Reaction equation

HRID 1848173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:22]([O-])=O)=[C:7]([CH:21]=1)[NH:8][CH2:9][C:10]1[CH:20]=[CH:19][C:13]2[N:14]=[C:15]([S:17][CH3:18])[O:16][C:12]=2[CH:11]=1.CC(O)=O.CO>C(Cl)Cl.[Zn]>[CH3:1][O:2][C:3]1[CH:21]=[C:7]([NH:8][CH2:9][C:10]2[CH:20]=[CH:19][C:13]3[N:14]=[C:15]([S:17][CH3:18])[O:16][C:12]=3[CH:11]=2)[C:6]([NH2:22])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 866811425-methoxy-N-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)-2-nitroaniline

Product 1

HCID 866811435-methoxy-N1-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)benzene-1,2-diamineYield 95.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methoxy-N-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)-2-nitroaniline (1.05 g, 3.05 mmol), HOAc (3.6 mL) and methanol (3.6 mL) in DCM (40 mL) at 0° C. was added zinc dust (1.98 g, 30.5 mmol) portionwise. After stirring for 2 h, the mixture was filtered. The filtrate was washed with aq NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to give 5-methoxy-N1-((2-(methylthio)benzo[d]oxazol-6-yl)methyl)benzene-1,2-diamine as a light yellow solid (920 mg, 95.7%). 1H NMR (300 MHz, DMSO-d6) δ 7.55-7.60 (m, 2H), 7.35 (d, J=7.8 Hz, 1H), 6.47 (d, J=8.1 Hz, 1H), 5.93-5.99 (m, 2H), 5.32 (t, 1H), 4.38 (d, J=5.7 Hz, 2H), 4.13 (s, 2H), 3.50 (s, 3H), 2.74 (s, 3H). LCMS (ESI) m/z 316 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with aq NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acb9f25d075d47268d654ad24ec564b2
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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