Benzylamine → HCID 18963768, compound

HRID 2226882Notes

Reaction equation

HRID 2226882 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:17]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:37][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:12])=[C:7]([O:13][CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 10587093HCID 10587093, compound

Product 1

HCID 18963768HCID 18963768, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-chloro-3-(1-methylethoxy)-2-benzofurancarboxylic acid (250 mg, 0.98 mmol) and 1,1'-carbonyldiimidazole (206 mg, 1.27 mmol) in 5 mL of tetrahydrofuran is heated at reflux for 1 hour. The reaction solution is cooled to room temperature and benzylamine (0.64 mL, 5.88 mmol) is added and stirring is continued at room temperature overnight. The reaction is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:2) provides 5-chloro-3-(1-methylethoxy)-N-(phenylmethyl)-2-benzofurancarboxamide in 79% yield; mp=80°-82° C.

Workup

  1. temperatureat reflux for 1 hour
  2. washwashed with brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography eluting with ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-385ca32712d1481dbb7167b8ac150beb
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

Loading…