Hydrochloric Acid → 2-Benzoylamino-3-cyano-4-tert.-butyl-thiophene

HRID 1733140Notes

Reaction equation

HRID 1733140 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]=1[C:16]#[N:17].Cl>C1(C)C=CC=CC=1>[C:1]([NH:10][C:11]1[S:12][CH:13]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:15]=1[C:16]#[N:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 5968662-Amino-4-(1,1-dimethylethyl)-3-thiophenecarbonitrile

Product 1

HCID 203003552-Benzoylamino-3-cyano-4-tert.-butyl-thiopheneYield 81.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After adding 29.4 g (0.21 mole) of benzoyl chloride, a mixture of 36 g (0.2 mole) of 2-amino-3-cyano-4-tert.-butyl-thiophene and 200 ml of toluene was boiled until the evolution of hydrogen chloride had ended (4 hours). Thereafter, the reaction mixture was filtered and the filtrate was concentrated on a rotary evaporator. The residue was recrystallized from methanol. 46.4 g of 2-benzoylamino-3-cyano-4-tert.-butyl-thiophene of melting point 130° C. were obtained in this manner.

Workup

  1. custom(4 hours)
  2. filtrationThereafter, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-a346e0b9e8444844804981ccc737072b
Source dataset
uspto-grants-1980_12
Patent number
US04240820

Reaction notes

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