Thiophosgene → 4-[2-(Dimethylamino)ethoxy]phenyl isothiocyanate

HRID 1959099Notes

Reaction equation

HRID 1959099 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][N:11]([CH3:22])[CH2:12][CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.[C:23](Cl)(Cl)=[S:24]>O1CCCC1>[CH3:10][N:11]([CH3:22])[CH2:12][CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([N:19]=[C:23]=[S:24])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 81531DiisopropylethylamineHCID 64846554-[2-(Dimethylamino)ethoxy]aniline

Product 1

HCID 226409714-[2-(Dimethylamino)ethoxy]phenyl isothiocyanateYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (344 mg, 2.66 mmol, 2.4 eq.) was added with stirring to a solution of 4-[2-(dimethylamino)ethoxy]aniline (200 mg, 1.11 mmol, 1 eq.) in tetrahydrofuran (2 mL) at 0° C., and then thiophosgene (153 mg, 1.33 mmol, 1.2 eq.) was added dropwise with stirring. The reaction mixture was allowed to warm to room temperature with stirring, and stirred at room temperature for 40 minutes, during which a precipitate formed. The tetrahydrofuran was removed under vacuum, and the residue was dissolved in ethyl acetate and washed with brine (3×10 mL), then the ethyl acetate layer dried over magnesium sulfate and the ethyl acetate evaporated to give 4-[2-(dimethylamino)ethoxy]phenyl isothiocyanate (0.20 g) as a dark brown oil, which was used without further purification.

Workup

  1. stirringwith stirring
  2. stirringstirred at room temperature for 40 minutes, during which a precipitate
  3. customformed
  4. customThe tetrahydrofuran was removed under vacuum
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with brine (3×10 mL)
  7. dry with materialthe ethyl acetate layer dried over magnesium sulfate
  8. customthe ethyl acetate evaporated

Sources & evidence

ORD record
ord-1642c875ae5744ac8f2eb850edc2caac
Source dataset
uspto-grants-2013_04
Patent number
US08410163B2

Reaction notes

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