Thiophosgene → tert-Butyl 4-isothiocyanatobenzoate

HRID 1993825Notes

Reaction equation

HRID 1993825 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[C:4](C(C)(C)C)[CH:3]=1.C([O-])(O)=O.[Na+].[C:20](Cl)(Cl)=[S:21]>C(Cl)(Cl)Cl>[C:5]([O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([N:1]=[C:20]=[S:21])=[CH:10][CH:9]=1)([CH3:9])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 40472796HCID 40472796, compound

Product 1

HCID 4281352tert-Butyl 4-isothiocyanatobenzoateYield 185.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-Butyl-4-aminobenzoate 1, (25.0 gm, 129.4 mmol) was taken into CHCl3 (250 ml) and saturated NaHCO3 (100 ml) in ice bath. To the stirred mixture thiophosgene (9.9 ml, 129.4 mmol) was added dropwise, and stirring continued for another 90 min. at room temperature after addition was complete. The organic layer was washed with water, dried over Na2SO4, and further purified by column chromatography to provide 28.3 gm of 4-isothiocyanato-benzoic acid t-butyl ester 2.

Workup

  1. additionafter addition
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customfurther purified by column chromatography

Sources & evidence

ORD record
ord-b218d21d8b7646cd97bc28a3401d0abc
Source dataset
uspto-grants-2010_01
Patent number
US07652047B2

Reaction notes

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