Sulfuric Acid → 2-Amino-5-(4-cyanophenyl)-3-thiophenecarboxamide

HRID 900447Notes

Reaction equation

HRID 900447 reaction equation
C([NH:4][C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:8][C:9]=1[C:10]#[N:11])(=O)C.S(=O)(=O)(O)[OH:21]>C(O)C>[NH2:4][C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)=[CH:8][C:9]=1[C:10]([NH2:11])=[O:21]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 179309842-Acetylamino-3-cyano-5-(4-cyanophenyl)thiophene

Product 1

HCID 179309912-Amino-5-(4-cyanophenyl)-3-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Acetylamino-3-cyano-5-(4-cyanophenyl)thiophene (470 mg) was heated at reflux in ethanol (15 ml) and concentrated sulphuric acid (1.5 ml) for 2.5 h. The reaction mixture was cooled and concentrated under reduced pressure. The residue was basified with 2N sodium hydroxide, with cooling, and the product was filtered off and dried (360 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. temperaturewith cooling
  4. filtrationthe product was filtered off
  5. customdried (360 mg)

Sources & evidence

ORD record
ord-5fb4821a73ee402494799a1b34a3f425
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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