Potassium Carbonate → HCID 53233006, compound

HRID 1011644Notes

Reaction equation

HRID 1011644 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 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-formyl-3-nitro-benzoic acid methyl ester (14.1 g, 67.5 mmol), mercapto-acetic acid ethyl ester (8.17 mL, 74.2 mmol) and potassium carbonate (12.2 g, 87.7 mmol) in 100 mL of anhydrous DMF was heated at 50 degrees Celsius for about 6 hours. After cooling to rt, the mixture was poured into ice-water and the mixture was stirred for around 40 mins. The solid formed was collected, washed with water and dried to give benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester-6-methyl ester as a pale solid (16.1 g, 90.4%). MS: calc'd 265 (MH+), exp 265 (MH+). 1H NMR (CDCl3, 400 MHz), 8.60 (s, 1H), 8.09 (s, 1H), 8.06 (d, 1H, J=8.8 Hz), 7.93 (d, 1H, J=8.8 Hz), 4.45 (q, 2H, J=6.8 Hz), 4.0 (s, 3H), 1.50 (t, 3H, J=7.2 Hz).

Workup

  1. temperaturewas heated at 50 degrees Celsius for about 6 hours
  2. customThe solid formed
  3. customwas collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b2045bc4a5d44b11bfaba6fa51aaa779
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

Loading…