Phthalic Anhydride → HCID 19815432, compound

HRID 653872Notes

Reaction equation

HRID 653872 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:11]([CH2:12][OH:13])=[C:10]([Cl:14])[N:9]=[C:8]2[CH2:15][CH2:16][O:17][CH3:18])=[CH:4][CH:3]=1.[C:21]1(=[O:31])[O:26][C:24](=[O:25])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12>C(#N)C>[C:24]([C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[C:21]([NH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:11]([CH2:12][OH:13])=[C:10]([Cl:14])[N:9]=[C:8]2[CH2:15][CH2:16][O:17][CH3:18])=[CH:4][CH:3]=1)=[O:31])([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 19815453HCID 19815453, compound

Product 1

HCID 19815432HCID 19815432, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To an acetonitrile solution (12 mL) of 1-(4-aminobenzyl)-4-chloro-5-hydroxymethyl-2-(2-methoxyethyl)imidazole (150 mg, 0.51 mmol) was added an acetonitrile solution (2 mL) of phthalic anhydride (75 mg, 0.51 mmol). After stirring overnight at room temperature a light yellow precipitate was produced. The mixture was cooled to 0°, filtered with suction onto a fine fritted funnel and the solid was washed with cold acetonitrile, chloroform and finally ether (2 mL each) to afford 180 mg (80%) of light tan solid, m.p. 185°-186° (dec.). NMR (200 MHz, CDCl3 /CD3OD) δ 8.05-6.95 (m, 8H); 5.30 (s, 2H); 4.50 (s, 2H); 3.60 (t, 2H, 5Hz); 3.25 (s, 3H); 2.8 (t, 2H, 5Hz). Mass Spec. Calcd. for C22H18ClN3O3 (M-2H2O):4.07.1037. Found: 407.1031.

Workup

  1. customwas produced
  2. temperatureThe mixture was cooled to 0°
  3. filtrationfiltered with suction onto a fine fritted funnel
  4. washthe solid was washed with cold acetonitrile, chloroform and finally ether (2 mL each)
  5. customto afford 180 mg (80%) of light tan solid, m.p. 185°-186° (dec.)

Sources & evidence

ORD record
ord-ff0743f787424c7886720d9734a55286
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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