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

HRID 2098141Notes

Reaction equation

HRID 2098141 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-3990b8ea89984688b72f9e138d190cf3
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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