Hydrochloric Acid → HCID 66758458, compound

HRID 1507869Notes

Reaction equation

HRID 1507869 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=O.[C:19](#[N:21])[CH3:20].Cl>O1CCOCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[S:3][C:2]3[N:1]=[C:19]([CH3:20])[NH:21][C:7](=[O:9])[C:6]=3[CH:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 21529229Ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate

Product 1

HCID 66758458HCID 66758458, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.3 g, 1.13 mmol) and acetonitrile (0.56 ml, 11.3 mmol) in dioxane (4 ml) was added 4M HCl in dioxane (4 ml). The mixture was stirred at room temperature overnight. The solvents were removed under reduced pressure. The residue was diluted with water and made alcaline with a saturated aqueous sodium bicarbonate solution. The precipitate was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1) to yield the title compound as a white solid (0.29 g, 81%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried
  6. customThe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1)

Sources & evidence

ORD record
ord-09aa14ecb4f74aeb908e2d987912a610
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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