Water → HCID 20221037, compound

HRID 980843Notes

Reaction equation

HRID 980843 reaction equation
O.[C:2]1([CH:12]=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:14](O)(=[S:18])[CH:15](C)O.[CH:20]([O-:22])=O.[NH4+:23]>C1(C)C=CC=CC=1>[C:2]1([CH:12]2[NH:23][C:20](=[O:22])[CH:14]([CH3:15])[S:18]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 61951-NaphthaldehydeHCID 2723923Ammonium formateHCID 178473673HCID 178473673, compound

Product 1

HCID 20221037HCID 20221037, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask with a trap for continuous collection and removal of water, 31 g (0.19 mole) 1-naphthaldehyde, 21.5 g (0.19 mole) 95% thiolactic acid, 12 g (0.19 mole) ammonium formate and 200 ml toluene were combined. The mixture was heated to reflux and refluxed three hours. The reaction mixture was allowed to cool and then filtered. The solids were washed with petroleum ether and then ethyl ether and then air-dried to give 29 g of the above-identified product as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed three hours
  4. temperatureto cool
  5. filtrationfiltered
  6. washThe solids were washed with petroleum ether
  7. dry with materialethyl ether and then air-dried

Sources & evidence

ORD record
ord-e0872134c4ae41d0ac7284fe2d63dec5
Source dataset
uspto-grants-1987_01
Patent number
US04639460

Reaction notes

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