Thiophosgene → Methyl 4-isothiocyanatothiophene-3-carboxylate

HRID 1978862Notes

Reaction equation

HRID 1978862 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1.[C:12](Cl)(Cl)=[S:13].C(=O)(O)[O-].[Na+]>O.ClCCl>[N:2]([C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1)=[C:12]=[S:13]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 2777609Methyl 4-aminothiophene-3-carboxylate Hydrochloride

Product 1

HCID 23259576Methyl 4-isothiocyanatothiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

19.4 g of methyl 4-aminothiophen-3-carboxylate hydrochloride were added to a suspension of 7.7 ml of thiophosgene and 18.5 g of sodium bicarbonate in 70 ml of water and 200 ml of dichloromethane at room temperature in the course of 30 minutes, and stirring was carried out for 1 hour at room temperature. After separation of the phases, the aqueous phase was extracted once with dichloromethane and the combined organic phases were washed once with water, dried over sodium sulfate and evaporated down.

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous phase was extracted once with dichloromethane
  3. washthe combined organic phases were washed once with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-ac2311a495f74cd18536f858cc4d5028
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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