Methyl Anthranilate → HCID 59533413, compound

HRID 880737Notes

Reaction equation

HRID 880737 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=C[CH:8]=1)[NH2:4].[F:12][C:13]([F:23])([F:22])[C:14]1[N:15]=[C:16]([C:19](Cl)=[O:20])[S:17][CH:18]=1.O1[CH2:29][CH2:28][O:27][CH2:26]C1>>[CH3:11][O:10][C:1](=[O:9])[C:2]1[CH:8]=[CH:29][C:28]([O:27][CH3:26])=[C:5]([CH3:6])[C:3]=1[NH:4][C:19]([C:16]1[S:17][CH:18]=[C:14]([C:13]([F:23])([F:22])[F:12])[N:15]=1)=[O:20]

Participants

4

Reactant 3

HCID 8635Methyl AnthranilateHCID 312751,4-Dioxane2×HCID 58282673HCID 58282673, compound

Product 1

HCID 59533413HCID 59533413, compoundYield 81%

Procedure

Under nitrogen atmosphere, a solution of methyl anthranilate (2 g, 1 eq.) in 1,4-dioxane (30 mL) was added at 0° C. to a solution of 4-trifluoromethyl-thiazole-2-carbonyl chloride (4.36 g, 2 eq.) in 1,4-dioxane (65 mL). The reaction mixture was stirred at room temperature for 16 hrs. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (DCM/MeOH) to yield compound 204 as a white solid in 81% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.51 (s, 3H), 3.80 (s, 3H), 3.85 (s, 3H), 6.75 (d, J=8.75 Hz, 1H), 7.87 (d, J=8.75 Hz, 1H), 7.95 (s, 1H), 10.48 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-b19947e7067345eebd87695a1e42b2b4
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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