Phthalic Anhydride → 3-[1-(4-(2-Carboxybenzamido)benzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

HRID 466448Notes

Reaction equation

HRID 466448 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]([CH2:12][CH:13]=[CH:14][OH:15])=[C:10]([Cl:16])[N:9]=[C:8]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.[C:23]1(=[O:33])[O:28][C:26](=[O:27])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12>C(Cl)(Cl)Cl.CCOCC>[C:26]([C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]([CH2:12][CH:13]=[CH:14][OH:15])=[C:10]([Cl:16])[N:9]=[C:8]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:21][CH:22]=1)=[O:33])([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 665771723-[1-(4-Aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Product 1

HCID 665771683-[1-(4-(2-Carboxybenzamido)benzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 95 mg of 3-[1-(4-aminobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol in 2 mL of CHCl3 was added 45 mg of phthalic anhydride and the mixture was stirred at room temperature for 1 hour. During this period of time the initially clear solution became turbid and produced solid. The reaction mixture was diluted with 2 mL of ether and the solid was collected by filtration and washed with ether. The desired product was obtained as a tan solid, 115 mg, m.p. 150°-151°; NMR (10% DMSO-d6 /CDCl3): δ 9.94 (s, 1 h); 7.71 and 6.93 (d, 4H, J=8.3 Hz); 6.36 (m, 2H); 5.1 (s, 2H); 4.18 (d, 2H, J=3.9 Hz); 2.6 (t, 3H, J=7.4 Hz); 1.68 (m, 2H); 1.34 (m, 2H); 0.89 (t, 3H, J=7.4 Hz).

Workup

  1. waitDuring this period of time the initially clear solution became
  2. customturbid and produced solid
  3. filtrationthe solid was collected by filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-a97b37b74a20400fb42fd95abadcd907
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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