HCID 68754553, compound → 5-Amino-4-(thiazol-2-yl)thiophene-3-carbonitrile

HRID 1519920Notes

Reaction equation

HRID 1519920 reaction equation
[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[S:12][CH:13]=[CH:14][N:15]=1)([O-])=O>[Fe].CC(O)=O>[NH2:1][C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[S:12][CH:13]=[CH:14][N:15]=1

Participants

4

Reactant 1

HCID 68754553HCID 68754553, compound

Product 1

HCID 687563605-Amino-4-(thiazol-2-yl)thiophene-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A 30 mL reaction vial was charged with 5-nitro-4-(thiazol-2-yl)thiophene-3-carbonitrile (180 mg, 0.76 mmol) and AcOH (3 mL). A spatula tip of iron dust was added and the reaction vial was heated to 60° C. for 20 min. The reaction mixture was cooled to 23° C. and partitioned between methylene chloride and sodium bicarbonate solution. The organic solution was dried over sodium sulfate and concentrated to give 5-amino-4-(thiazol-2-yl)thiophene-3-carbonitrile as a red solid. LCMS showed an m/z of 208.0 with a retention time of 2.016 min using method [1].

Workup

  1. customA 30 mL reaction
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled to 23° C.
  4. custompartitioned between methylene chloride and sodium bicarbonate solution
  5. dry with materialThe organic solution was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae0b52f53d114938a45718e6262b419d
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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