Maleic Anhydride → HCID 21875228, compound

HRID 2110449Notes

Reaction equation

HRID 2110449 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:15]1(=O)[O:20][C:18](=[O:19])[CH:17]=[CH:16]1>C(O)(=O)C>[F:12][C:11]([F:14])([F:13])[C:9]1[O:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([N:1]3[C:18](=[O:19])[CH:17]=[CH:16][C:15]3=[O:20])[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 218752592-(Trifluoromethyl)-4-benzoxazolamine

Product 1

HCID 21875228HCID 21875228, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 476B (0.500 g, 2.48 mmol) was dissolved in acetic acid (10 mL) and maleic anhydride (0.267 g, 2.72 mmol) was added. The mixture was heated at reflux for 3 h, cooled and the solvent removed in vacuo to give a tan solid. The crude product was purified by flash chromatography on silica gel eluting with 2% MeOH/CH2Cl2 to give compound 476C (0.40 g, 57%) as an off-white solid. HPLC: 89.7% at 2.38 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 283.21 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. customto give a tan solid
  6. customThe crude product was purified by flash chromatography on silica gel eluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-33db7f00a0b0412684370ce69268cdac
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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