Triethylamine → HCID 67098447, compound

HRID 2079291Notes

Reaction equation

HRID 2079291 reaction equation
N[C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([N:14](CC)CC)C.[C:19](Cl)(=[O:28])[C:20]1[C:21]([O:26][CH3:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.Cl.C(N(CC)CC)C>C1COCC1>[C:19]([C:2]1[C:10]([NH2:14])=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])(=[O:28])[C:20]1[C:21]([O:26][CH3:27])=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 889692-Methoxybenzoyl chlorideHCID 50192712-Amino-5-bromobenzamide

Product 1

HCID 67098447HCID 67098447, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-bromo-benzamide (29.2 g, 136 mmol) and triethylamine (25.0 mL, 173 mmol) in THF (500 mL) was added dropwise o-anisoyl chloride (24.0 g, 140 mmol). Stirring at room temperature was continued for 3 h, after which the formed precipitate was filtered and washed once with THF and twice with dichloromethane yielding 2-(o-anisoyl)-amino-5-bromo-benzamide (51.4 g, 84%) with 1 equivalent of triethylamine hydrochloride.

Workup

  1. filtrationafter which the formed precipitate was filtered
  2. washwashed once with THF and twice with dichloromethane

Sources & evidence

ORD record
ord-c9b8c36352214617be563af66af98870
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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