Benzenepropanoyl chloride → HCID 3615712, compound

HRID 1037625Notes

Reaction equation

HRID 1037625 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=[O:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOCC>[Br:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 3615712HCID 3615712, compoundYield 882.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Amino-5-bromobenzoic acid (2.0 g, 9.3 mmol, 1.8 equiv) in ether (50 mL) was treated with hydrocinnamoyl chloride (760 uL, 0.51 mmol, 1.0 equiv) and stirred overnight. The solution was filtered and washed sparingly with ether. The filtrate, upon concentration, gave a white amorphous powder which was recrystallized from ethanol/water to give fine yellowish needles of 5-bromo-2-(3-phenylpropanamido)benzoic acid (1.58 g, 4.5 mmol, 89%). This material (1.58 g, 4.5 mmol, 1.0 equiv) was added to acetic anhydride (8 mL) and heated to 100° C. for 30 min. to dissolve all the material, then 160° C. until ca. 20% of the volume had distilled. The reaction mixture was then concentrated in vacuo to provide 6-bromo-2-phenethyl-benzo[3,1]oxazin-4-one as a yellowish waxy solid.

Workup

  1. filtrationThe solution was filtered
  2. washwashed sparingly with ether
  3. concentrationThe filtrate, upon concentration
  4. customgave a white amorphous powder which
  5. customwas recrystallized from ethanol/water

Sources & evidence

ORD record
ord-eaa9890947ff41d3bbc5659aa18096b3
Source dataset
uspto-grants-2013_10
Patent number
US08546564B2

Reaction notes

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