Water → methyl 3-isothiocyanatothiophene-2-carboxylate

HRID 2063507Notes

Reaction equation

HRID 2063507 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O-:13])=[O:12].[CH2:14](N(CC)CC)C.O>O1CCCC1.C(OCC)C>[N:5]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])=[C:1]=[S:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 22256629HCID 22256629, compound

Product 1

HCID 2777461methyl 3-isothiocyanatothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Thiophosgene (1.1 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C. of 3-amino-2-thiophenecarboxylate (2 g, 1 eq) and triethylamine (3.9 g, 3 eq) in tetrahydrofuran (100 ml). The mixture is stirred for 15 min at 0° C. then water (70 ml) and diethyl ether (150 ml) are added. After decantation and extractions, the organic phases are combined, washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue by flash chromatography on silica gel (eluent:heptane 100% to heptane/ethyl acetate 7:3) produces the expected compound in the form of a beige powder (2.15 g, 85% yield).

Workup

  1. extractionAfter decantation and extractions
  2. washwashed with salt water
  3. dry with materialdried over Na2SO4
  4. concentrationthen concentrated under reduced pressure at 40° C
  5. customPurification of the residue by flash chromatography on silica gel (eluent:heptane 100% to heptane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-18140c29418e420bb3f592360b99583c
Source dataset
uspto-grants-2012_10
Patent number
US08288395B2

Reaction notes

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