1-(2-Hydroxy-3-nitrophenyl)-3-mesitylthiourea → N-Mesityl-7-nitro-1,3-benzoxazol-2-amine

HRID 2235528Notes

Reaction equation

HRID 2235528 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])=S>C(#N)C.C(OCC)(=O)C.[Hg](Cl)Cl>[C:16]1([CH3:23])[CH:17]=[C:18]([CH3:22])[CH:19]=[C:20]([CH3:21])[C:15]=1[NH:14][C:12]1[O:1][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=2[N:11]=1

Participants

5

Reactant 1

HCID 860491261-(2-Hydroxy-3-nitrophenyl)-3-mesitylthiourea

Product 1

HCID 68581419N-Mesityl-7-nitro-1,3-benzoxazol-2-amineYield 90%

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 0.06 g (0.18 mmol) of 1-(2-hydroxy-3-nitrophenyl)-3-mesitylthiourea in acetonitrile was added 0.10 g (0.36 mmol) of mercury (II) chloride, and the mixture was then stirred for 1 h. The reaction mixture was diluted with ethyl acetate (2 ml) and filtered through a prepacked celite column. The filtrate was concentrated under reduced pressure and the residue was purified via Biotage chromatography eluting with 20% ethyl acetate/dichloromethane to afford 0.047 g (90%) of product.

Workup

  1. filtrationfiltered through a prepacked celite column
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified via Biotage chromatography
  4. washeluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-b4f8b17b19644018977ece0c475c6802
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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