Potassium Carbonate → HCID 53233006, compound

HRID 548220Notes

Reaction equation

HRID 548220 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[C:6]([N+]([O-])=O)[CH:5]=1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20][SH:21])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[CH:10]=[C:20]([C:19]([O:18][CH2:16][CH3:17])=[O:22])[S:21][C:6]=2[CH:5]=1)=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Product 1

HCID 53233006HCID 53233006, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-formyl-3-nitrobenzoic acid methyl ester (3.9 g, 18.7 mmol), mercapto-acetic acid ethyl ester (2.2 mL, 20.4 mmol) and K2CO3 (3.3 g, 24 mmol) in DMF (40 ml, 10 vol) was heated to 50° C. overnight. After cooling to r.t. the mixture was poured onto ice-cold water (250 mL) and the resulting mixture stirred for 40 min. The solid formed was isolated by filtration, washed with water (4×50 mL) and dried under vacuum to afford the title compound (3.9 g, 80%). LCMS m/z 265 [M++H]+, 1H NMR (300 MHz, CDCl3) δ: 1.40 (3H, t J=6.8 Hz, CH3), 3.95 (3H, s, OMe), 4.40 (2H, q J 7.2 Hz, CH2), 7.88 (1H, d J=8.0 Hz, ArH), 7.97-8.09 (2H, m. ArH), 8.56 (1H, s, ArH).

Workup

  1. temperatureAfter cooling to r.t. the mixture
  2. additionwas poured onto ice-cold water (250 mL)
  3. customThe solid formed
  4. customwas isolated by filtration
  5. washwashed with water (4×50 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c8562e4a93ef45caa347a772ed6a457d
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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