Sodium Carbonate → 1-(2-Hydroxy-3-nitrophenyl)-3-mesitylthiourea

HRID 2235527Notes

Reaction equation

HRID 2235527 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].C(=O)([O-])[O-].[Na+].[Na+].[N:18]([C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=1[CH3:29])=[C:19]=[S:20]>C(O)C>[OH:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:19]([NH:18][C:21]1[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27])=[S:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 51272912-Amino-6-nitrophenol

Product 1

HCID 860491261-(2-Hydroxy-3-nitrophenyl)-3-mesitylthioureaYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture containing 0.10 g (0.65 mmol) of 2-amino-6-nitrophenol and 0.14 g (1.3 mmol) of sodium carbonate in ethanol was added 0.14 g (0.78 mmol) of 2-isothiocyanato-1,3,5-trimethylbenzene. The reaction was heated at reflux overnight. The reaction was cooled to room temperature, filtered and concentrated under reduced pressure. Purification of the residue via Biotage chromatography eluting with 20% ethyl acetate/dichloromethane gave 0.17 g (80%) of product.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue via Biotage chromatography
  6. washeluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-ea49320adf23480fb933addb75db13d1
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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