Stannous chloride dihydrate → 5-Amino-4-(thiazol-4-yl)thiophene-3-carbonitrile

HRID 1519927Notes

Reaction equation

HRID 1519927 reaction equation
[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[N:12]=[CH:13][S:14][CH:15]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:1][C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[N:12]=[CH:13][S:14][CH:15]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 68754106HCID 68754106, compound

Product 1

HCID 687545655-Amino-4-(thiazol-4-yl)thiophene-3-carbonitrileYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-nitro-4-(thiazol-4-yl)thiophene-3-carbonitrile (0.071 g, 0.31 mmol) in ethyl acetate (3 mL) was added tin (II) chloride dihydrate (0.29 g, 1.27 mmol). The reaction mixture was heated in an oil bath set at 70° C. under condenser. After 20 min. the mixture was cooled to RT and concentrated under reduced pressure. Purification by flash chromatography (silica, 40:60 ethyl acetate/hexane) gave 5-amino-4-(thiazol-4-yl)thiophene-3-carbonitrile (24 mgs, 38%) Retention time (min)=1.837, method [4], MS(ESI) 208.0 (M+H).

Workup

  1. temperatureThe reaction mixture was heated in an oil bath
  2. customset at 70° C. under condenser
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 40:60 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b40b15d1c8f849ea9bdfecafab64f37c
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

Loading…