2-Nitrobenzaldehyde → Methyl 2,3,3a,4,7,7a-hexahydro-3a-hydroxy-5-methyl-7-(2-nitrophenyl)-1,1-dioxo-thieno[3,2-b]pyridine-6-carboxylate

HRID 1638365Notes

Reaction equation

HRID 1638365 reaction equation
[CH2:1]1[C:7](=[O:8])[CH2:6][S:3](=[O:5])(=[O:4])[CH2:2]1.[N+:9]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=O)([O-:11])=[O:10].[NH2:20]/[C:21](/[CH3:27])=[CH:22]\[C:23]([O:25][CH3:26])=[O:24]>C(O)C>[OH:8][C:7]12[CH2:1][CH2:2][S:3](=[O:5])(=[O:4])[CH:6]1[CH:14]([C:13]1[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=1[N+:9]([O-:11])=[O:10])[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:27])[NH:20]2

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 14280858Methyl 2,3,3a,4,7,7a-hexahydro-3a-hydroxy-5-methyl-7-(2-nitrophenyl)-1,1-dioxo-thieno[3,2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution fo tetrahydrothiophene-3-oxo-1,1-dioxide (1.3 g, 0.01 moles), 2-nitrobenzaldehyde (1.5 g, 0.01 moles) and methyl 3-aminocrotonate (1.1 g, 0.01 moles) in ethanol (20 mL) was stirred overnight. The resulting crystals were isolated by filtration and washed 2x with ethanol and 2x with diethyl ether. After drying under high vacuum for 24 hours 2.54 g of product was obtained, mp 175°-179° C. (dec).

Workup

  1. customThe resulting crystals were isolated by filtration
  2. washwashed 2x with ethanol and 2x with diethyl ether
  3. dry with materialAfter drying under high vacuum for 24 hours 2.54 g of product
  4. customwas obtained

Sources & evidence

ORD record
ord-8aff05f4ef864ab4ae791272768a3dd7
Source dataset
uspto-grants-1989_11
Patent number
US04879384

Reaction notes

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