2,4,6-Trimethylphenyl isothiocyanate → 1-[3-(tert-Butyldimethylsilyloxymethyl)phenyl]-3-mesitylthiourea

HRID 2235521Notes

Reaction equation

HRID 2235521 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:17]1([CH3:28])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[N:25]=[C:26]=[S:27]>CO>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:13][C:26]([NH:25][C:18]2[C:17]([CH3:28])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=2[CH3:24])=[S:27])[CH:14]=[CH:15][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1386592,4,6-Trimethylphenyl isothiocyanateHCID 105859773-(Tert-butyldimethylsilyloxymethyl)aniline

Product 1

HCID 875051471-[3-(tert-Butyldimethylsilyloxymethyl)phenyl]-3-mesitylthiourea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.45 g (1.9 mmol) of 3-(tert-butyldimethylsilyloxymethyl)aniline in 3 mL of methanol was added 0.67 g (3.8 mmol) of mesitylisothiocyanate. The mixture was heated at reflux for 18 h. The mixture was concentrated and purified by flash chromatography eluting with a 16% ethyl acetate/hexanes mixture to give 0.56 (71%) of the title compound as a sticky white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationThe mixture was concentrated
  4. custompurified by flash chromatography
  5. washeluting with a 16% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-6547296492e3401eb7f05e40db9ad8fd
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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