Hydrogen Peroxide → 4-Carbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29293Notes

Reaction equation

HRID 29293 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].C([O-])([O-])=[O:19].[Na+].[Na+].OO>C(O)C.CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:19])[NH2:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 687167794-Cyano-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687150404-Carbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To 213 mg of 4-cyano-3-methyl-benzofuran-2-carboxylic acid ethyl ester (Example 20, Step 2) in 6 mL of ethanol and 6 mL of DMSO was added 3 mL of Na2CO3 (3M), followed by 3 mL of H2O2 (30% in water). After 24 h of reaction, the mixture was worked up to give 4-carbamoyl-3-methyl-benzofuran-2-carboxylic acid ethyl ester in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.4 (t, J=7.1 Hz, 3 H) 2.6 (s, 3 H) 4.4 (q, J=7.1 Hz, 2 H) 7.4 (dd, J=7.3, 1.0 Hz, 1 H) 7.5 (dd, J=8.3, 7.3 Hz, 1 H) 7.7 (s, 1 H) 7.8 (m, 1 H) 8.0 (s, 1 H).

Workup

  1. customAfter 24 h of reaction

Sources & evidence

ORD record
ord-4fbd687bc1344138a3c95173a039e488
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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