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 247133Notes

Reaction equation

HRID 247133 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 of 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 2× with ethanol and 2× 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 2× with ethanol and 2× 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-f8dd25fbbbbd4b21992a8cc18357a83f
Source dataset
uspto-grants-1987_11
Patent number
US04705785

Reaction notes

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