Thiophosgene → 1-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidine

HRID 1713632Notes

Reaction equation

HRID 1713632 reaction equation
[C:1](Cl)(Cl)=[S:2].[N:5]1([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[N:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:18][CH:17]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Product 1

HCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of thiophosgene (150 μL, 1.76 mmol, 1.2 equiv) in CHCl3 (2.7 mL) is added to a vigorously stirred mixture of 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (0.303 g, 1.47 mmol) in CHCl3 (7.5 mL) and a saturated aqueous solution of NaHCO3 (7.5 mL). The resulting dark mixture is stirred at RT for 1 h. The layers are separated and the aqueous phase is extracted with CHCl3. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a dark oil: ES-MS: 249.0 [M+H]+; single peak at tR=6.90 min (System 1).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with CHCl3
  3. washThe organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baf72dacde2b4e3687d2fe847b434c28
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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