Sulfuric Acid → n-(2,6-Dichloro-4-carboxyphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide

HRID 322034Notes

Reaction equation

HRID 322034 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:28][CH3:29])=[C:20]2[O:24][C:23]([CH:25]([CH3:27])[CH3:26])=[CH:22][C:21]=12)=[O:15].S(=O)(=O)(O)O>C(O)COCCO.[OH-].[Na+].O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:28][CH3:29])=[C:20]2[O:24][C:23]([CH:25]([CH3:27])[CH3:26])=[CH:22][C:21]=12)=[O:15]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 22009528n-(2,6-Dichloro-4-methoxycarbonylphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide

Product 1

HCID 22009534n-(2,6-Dichloro-4-carboxyphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3.7 g of N-(2,6-Dichloro-4-methoxycarbonylphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide are refluxed for 15 min. in 20 ml of diethylene glycol and 30 ml of water in which 0.41 g of caustic soda is dissolved. The solution is diluted with water and acidified to pH 2 using 2 N sulfuric acid. The product precipitates in this process. It is filtered off with suction on a suction filter, washed free of acid with water and dried in vacuo: m.p. 279° C.

Workup

  1. customThe product precipitates in this process
  2. filtrationIt is filtered off with suction on a suction
  3. filtrationfilter
  4. washwashed free of acid with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7fd1b9e472fd42ef9f2819e08ce2b609
Source dataset
uspto-grants-2001_04
Patent number
US06211203B1

Reaction notes

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