Methanol → 5-Bromobenzofuran-2-carboxylic Acid Dibenzylamide

HRID 1860624Notes

Reaction equation

HRID 1860624 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([C:25](Cl)=[O:26])=[CH:22][C:21]=2[CH:28]=1.CO>C1(C)C=CC=CC=1>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:25]([C:23]1[O:24][C:20]2[CH:19]=[CH:18][C:17]([Br:16])=[CH:28][C:21]=2[CH:22]=1)=[O:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7656DibenzylamineHCID 27955345-Bromobenzo[b]furan-2-carbonyl chloride

Product 1

HCID 98667995-Bromobenzofuran-2-carboxylic Acid DibenzylamideYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
105 °C

Procedure

A solution of 50 ml of toluene and 7.9 g of dibenzylamine are added dropwise with stirring at 50-60° C. in the course of 10 min. to 5.2 g of 5-bromobenzofuran-2-carbonyl chloride in 100 ml of toluene. A colourless solid is obtained. After dropwise addition is complete, the mixture is additionally stirred at 100-110° C. for a further 3 hours. After cooling to 10° C., the solid product (dibenzylammonium chloride) is filtered off with suction. The filtrate is then treated with a mixture of 150 ml of water and 10 g of sodium carbonate and thoroughly shaken. The organic phase is separated off, washed again with 100 ml of water, dried using sodium sulfate and filtered. The, filtrate is concentrated on a Rotavapor in vacuo to a residue (residue: 9.5 g). After recrystallization from 100 ml of methanol, 6.5 g of product (yield 77%) remain after isolation.

Workup

  1. customA colourless solid is obtained
  2. additionAfter dropwise addition
  3. temperatureAfter cooling to 10° C.
  4. filtrationthe solid product (dibenzylammonium chloride) is filtered off with suction
  5. additionThe filtrate is then treated with a mixture of 150 ml of water and 10 g of sodium carbonate
  6. stirringthoroughly shaken
  7. customThe organic phase is separated off
  8. washwashed again with 100 ml of water
  9. customdried
  10. filtrationfiltered
  11. concentrationThe, filtrate is concentrated on a Rotavapor in vacuo to a residue (residue: 9.5 g)

Sources & evidence

ORD record
ord-04f5167b96d845589dad789600f3e056
Source dataset
uspto-grants-2003_03
Patent number
US06531503B1

Reaction notes

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