Hexamethylenetetramine → 5-Formylthiophene-2-Carbonitrile

HRID 1198184Notes

Reaction equation

HRID 1198184 reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.CC1SC(C#N)=CC=1.BrN1C(=[O:24])CCC1=O.C1N2CN3CN(C2)CN1C3>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(O)(=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[C:8]([C:6]1[S:7][C:3]([CH:2]=[O:24])=[CH:4][CH:5]=1)#[N:9]

Participants

10

Reactant 4

HCID 4101HexamethylenetetramineHCID 67184N-bromobutanimideHCID 3127335-Methylthiophene-2-carbonitrileHCID 105600165-(Bromomethyl)thiophene-2-carbonitrile

Product 1

HCID 122800045-Formylthiophene-2-CarbonitrileYield 44.8%

Reagents, catalysts & solvents 5

HCID 7187Benzoyl PeroxideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

8 g of 5-bromomethylthiophene-2-carbonitrile (prepared by brominating 5.7 g of 5-methylthiophene-2-carbonitrile and 8.42 g of N-bromosuccinimide in 68 ml of carbon tetrachloride under exposure to light and with the addition of 185 mg of benzoyl peroxide) is refluxed for 30 minutes in 35 ml of chloroform with 5.6 g of hexamethylenetetramine. The precipitated salt is suctioned off and refluxed in 30 ml of acetic acid and 30 ml of water for 2 hours. After extraction with ether, washing of the ether phase with water, drying, and evaporation, 2.43 g of 5-cyanothiophene-2-aldehyde is obtained.

Workup

  1. extractionAfter extraction with ether
  2. washwashing of the ether phase with water
  3. customdrying
  4. customevaporation

Sources & evidence

ORD record
ord-d1535dd1bad849a983af595cdf90a1c0
Source dataset
uspto-grants-1994_01
Patent number
US05280035

Reaction notes

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