Isatoic Anhydride → HCID 7064003, compound

HRID 1864044Notes

Reaction equation

HRID 1864044 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.C(N(CC)CC)C.Cl.[F:21][C:22]([F:26])([F:25])[CH2:23][NH2:24]>O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:24][CH2:23][C:22]([F:26])([F:25])[F:21])=[O:4]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochloride

Product 1

HCID 7064003HCID 7064003, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round-bottomed flask was charged with isatoic anhydride (5.0 g, 0.030 mol), 15 mL water, and triethylamine (4.69 mL, 0.033 mol). (2,2,2-trifluoroethyl)amine hydrochloride (4.98 g, 0.036 mol) was added slowly to the reaction mixture. After 16 h, the reaction mixture was concentrated to dryness. The crude product was purified silica gel column (EtOAc/Hexanes) to afford the title compound as a white solid (3.42 g, 51%): Mass (M+H)+=120, 219.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customThe crude product was purified silica gel column (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-0bea212a8e07482f9239baee660e136a
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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