Pyridine → N-[2-(aminocarbonyl)phenyl]-2,3-dihydro-1-benzofuran-5-carboxamide

HRID 1991445Notes

Reaction equation

HRID 1991445 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]1=2.S(Cl)(Cl)=O.[C:17]([NH2:26])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:20].N1C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:26][C:17]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][C:10]([C:7]1[CH:8]=[CH:9][C:2]2[O:1][CH2:5][CH2:4][C:3]=2[CH:6]=1)=[O:12])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6942AnthranilamideHCID 24386Thionyl ChlorideHCID 6765832,3-Dihydrobenzo(b)furan-5-carboxylic acid

Product 1

HCID 51077261N-[2-(aminocarbonyl)phenyl]-2,3-dihydro-1-benzofuran-5-carboxamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (1.0 g, 6.1 mmol) in thionyl chloride (2.2 mL, 30.5 mmol) is stirred at room temperature for 4 h. The volatiles were removed by evaporation. To a solution of the residue and anthranilamide (750 mg, 5.5 mmol) in CHCl3 (30 mL) is added pyridine (670 □L, 8.3 mmol) and the mixture stirred at room temperature for 18 h. The volatiles were removed by evaporation and the residue is partitioned between EtOAc and 1 N sodium carbonate. The resulting precipitate that formed between the aqueous and organic phases is collected by filtration and dried under vacuum to afford the desired intermediate (1.5 g, 5.3 mmol; 87% yield); ); Rf=0.31 (EtOAc/hexanes, 95/5); mp=230-235° C.; ES MS(M+H)+=283.

Workup

  1. customThe volatiles were removed by evaporation
  2. stirringthe mixture stirred at room temperature for 18 h
  3. customThe volatiles were removed by evaporation
  4. customthe residue is partitioned between EtOAc and 1 N sodium carbonate
  5. customThe resulting precipitate that formed between the aqueous and organic phases
  6. filtrationis collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5494e16966024e33b1818501f9bce2a3
Source dataset
uspto-grants-2010_01
Patent number
US07645878B2

Reaction notes

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