Formic Acid → 2-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile

HRID 1591289Notes

Reaction equation

HRID 1591289 reaction equation
CN(C)C=[N:4][C:5]1[S:6][C:7]([CH:13]=[O:14])=[C:8]([Cl:12])[C:9]=1[C:10]#[N:11].C(O)=O>O>[NH2:4][C:5]1[S:6][C:7]([CH:13]=[O:14])=[C:8]([Cl:12])[C:9]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 54382946N'-(4-chloro-3-cyano-5-formyl-2-thienyl)-N,N-dimethylformamidine

Product 1

HCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48.3 parts of N,N-dimethyl-N'-(4-chloro-3-cyano-5-formylthien-2-yl)-formamidine in a mixture of 200 parts of formic acid and 200 parts of water are heated at the boil for 3 hours. After the mixture has cooled to room temperature, the product is filtered off under suction, washed with water and dried. 33.5 parts (90% of theory) of 2-amino-4-chloro-3-cyano-5-formylthiophene are obtained. Decomposition temperature: 270° C. (from glacial acetic acid), IR (KBr): 3377, 3298, 3156 (NH2), 2216 (C≡N), 1623 cm-1 (C=0).

Workup

  1. temperatureare heated at the boil for 3 hours
  2. filtrationthe product is filtered off under suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f6503d4ad621412186de212853a8b31d
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

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