3-Nitrobenzaldehyde → 2-Hydroxyethyl 3,4,5,8-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano [3,2-b]pyridine-7-carboxylate

HRID 867942Notes

Reaction equation

HRID 867942 reaction equation
[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11].[OH:21][CH2:22][CH2:23][O:24][C:25](=[O:30])/[CH:26]=[C:27](\[NH2:29])/[CH3:28].C([O-])(=O)C.[NH4+]>C(O)C>[CH3:28][C:27]1[NH:29][C:3]2[CH2:4][CH2:5][CH2:6][S:1](=[O:9])(=[O:8])[C:2]=2[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[C:26]=1[C:25]([O:24][CH2:23][CH2:22][OH:21])=[O:30]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 517165Ammonium AcetateHCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxideHCID 19980851HCID 19980851, compound

Product 1

HCID 140112132-Hydroxyethyl 3,4,5,8-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano [3,2-b]pyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tetrahydrothiopyran-3-one-1,1-dioxide (2.80 g, 0.0189 moles), 3-nitrobenzaldehyde (2.85 g, 0.0189 moles), 2-hydroxyethyl-3-aminocrotonate (3.28 g, 0.0226 moles), ammonium acetate (0.291 g, 0.0038 moles) and ethanol (35 mL) was refluxed for 16 hours. After cooling to room temperature the resulting solid was isolated by filtration, washed with ethanol and diethyl ether. The product was dried under vacuum for 16 hours at room temperature affording the product; mp 233°-235° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. customwas isolated by filtration
  3. washwashed with ethanol and diethyl ether
  4. customThe product was dried under vacuum for 16 hours at room temperature
  5. customaffording the product

Sources & evidence

ORD record
ord-4ad23f1859264c5e83124e43e277b50c
Source dataset
uspto-grants-1988_10
Patent number
US04777167

Reaction notes

Loading…