HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexamethylenetetramine → 5-Formylthiophene-2-Carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexamethylenetetramine | HCID 4101 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 5-Methylthiophene-2-carbonitrile | HCID 312733 | — |
| Reactant | 5-(Bromomethyl)thiophene-2-carbonitrile | HCID 10560016 | — |
| Catalyst | Benzoyl Peroxide | HCID 7187 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 5-Formylthiophene-2-Carbonitrile | HCID 12280004 | 44.8% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05280035 |
| Source dataset | uspto-grants-1994_01 |
| ORD ID | ord-d1535dd1bad849a983af595cdf90a1c0 |
| Source note | uspto-grants-1994_01 |