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 247136Notes

Reaction equation

HRID 247136 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-231e5962c9404d32ae581c43e8e791ff
Source dataset
uspto-grants-1987_11
Patent number
US04705785

Reaction notes

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