Pyridine → 3-Thiophenecarbonitrile, 2-amino-4-chloro-

HRID 1591295Notes

Reaction equation

HRID 1591295 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH2:6][C:7]1[S:8][CH:9]=[C:10](O)[C:11]=1[C:12]#[N:13].N1C=CC=CC=1>O1CCCC1>[NH2:6][C:7]1[S:8][CH:9]=[C:10]([Cl:3])[C:11]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 135480882-Amino-4-hydroxythiophene-3-carbonitrile

Product 1

HCID 140290413-Thiophenecarbonitrile, 2-amino-4-chloro-Yield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.3 parts of phosphoryl trichloride are added to a mixture of 14 parts of 2-amino-3-cyano-4-hydroxythiophene, 7.9 parts of pyridine and 70 parts of tetrahydrofuran, and the mixture is then heated at the boil for 1 hour. After cooling, the mixture is poured onto water and left to stand overnight, and the precipitate is filtered off under suction, washed with water and dried. 9.4 parts (60% of theory) of 2-amino-4-chloro-3-cyanothiophene are obtained.

Workup

  1. temperaturethe mixture is then heated at the boil for 1 hour
  2. temperatureAfter cooling
  3. additionthe mixture is poured onto water
  4. waitleft
  5. filtrationthe precipitate is filtered off under suction
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bcf1b00a9c88428e8a4461a80d8edc6f
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

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