Methyl Anthranilate → HCID 59533413, compound

HRID 388648Notes

Reaction equation

HRID 388648 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-587ff642f94e4c4b8e23e4ddfc9c13f5
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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