Thiophosgene → HCID 22641003, compound

HRID 1091676Notes

Reaction equation

HRID 1091676 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)(O)[O-].[Na+].[C:21](Cl)(Cl)=[S:22]>C(Cl)(Cl)Cl.O>[N:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:10][CH:11]=1)=[C:21]=[S:22]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]aniline

Product 1

HCID 22641003HCID 22641003, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To an ice-cooled stirred biphasic solution of 4-[2-(1H-imidazol-1-yl)ethoxy]benzenamine (1.00 g; 4.92 mmol) and sodium bicarbonate (2.07 g; 24.6 mmol) in chloroform (100 mL) and water (50 mL) was added a solution of thiophosgene (452 μL; 5.90 mmol) in chloroform (10 mL) over 5 min. The mixture was stirred at ice-bath temperature for 20 min, and then the aqueous and organic phases were separated and the aqueous phase extracted with chloroform (50 mL). The combined chloroform layers were washed with brine, then dried over magnesium sulfate and concentrated under reduced pressure to give 1-[2-(4-isothiocyanatophenoxy)ethyl]-1H-imidazole (1.41 g) as a yellow oil.

Workup

  1. customthe aqueous and organic phases were separated
  2. extractionthe aqueous phase extracted with chloroform (50 mL)
  3. washThe combined chloroform layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6d10957b73843c5a00b7c791375be5f
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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