Dichloromethane → 1-t-Butoxycarbonyl-3,3-dimethylthiourea

HRID 724520Notes

Reaction equation

HRID 724520 reaction equation
[CH3:1][NH:2][C:3](=[NH:6])[S:4]C.[O:7](C(OC(C)(C)C)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=O.[CH2:22](Cl)Cl>C([O-])(O)=O.[Na+].O>[CH3:1][N:2]([CH3:22])[C:3](=[N:6][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])[SH:4]

Participants

6

Reactant 3

HCID 6344Dichloromethane2×HCID 90495Di-tert-butyl dicarbonateHCID 178485202HCID 178485202, compound

Product 1

HCID 450920251-t-Butoxycarbonyl-3,3-dimethylthiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

44 (1.04 g, 10.0 mmol) and BOC2O (2.18 g, 10.0 mmol) were dissolved in a biphasic solution of CH2Cl2 (40 mL) and sat. NaHCO3 (40 mL) and the two layers stirred vigorously. After 24 h, the reaction mixture was diluted with CH2Cl2 (60 mL), water (60 mL) and the organic layer separated. The organic layer was washed with water (2×100 mL), dried (Na2SO4) and concentrated. The product oil was purified over silica gel (20% EtOAc/Hexane) to give a mixture of isomers of the product mono-BOC protected S—Me-isothiourea as a sticky oil (1.85 g, 90%). 1H-NMR (DMSO-d6) 9.45 (s, 0.4H), 8.97 (s, 1H), 3.17 (s, 3H), 3.06 (s, 1.2H), 2.33 (s, 1.2H), 2.23 (s, 3H), 1.45 (s, 9H), 1.39 (s, 3.6H).

Workup

  1. customthe organic layer separated
  2. washThe organic layer was washed with water (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product oil was purified over silica gel (20% EtOAc/Hexane)
  6. customto give
  7. additiona mixture of isomers of the product mono-BOC

Sources & evidence

ORD record
ord-9d903c2057d04e659d394c33f037f25a
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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