Anthranilamide → HCID 4399936, compound

HRID 868904Notes

Reaction equation

HRID 868904 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[Cl:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>CC#N>[Cl:18][CH2:19][CH2:20][C:21]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])=[O:22]

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 8471TriethylamineHCID 693643-Chloropropionyl chloride

Product 1

HCID 4399936HCID 4399936, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-aminobenzamide (500 mg, 3.68 mmol) and triethylamine (NEt3) (450 mg, 4.41 mmol) in CH3CN (30 mL) was added 3-chloropropanoyl chloride (0.45 mL, 4.41 mmol) dropwise at room temperature. After stirring overnight, the reaction mixture was concentrated to give the desired product (800 mg) as solid, which was used for the next step without further purification. LC-MS: m/z 227 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f4595d23256f4edda29f9f475f720d1d
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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