3-(3-Chloro-propoxy)-benzoic acid ethyl ester → 3-[3-(3-Benzyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-propoxy]-benzoic acid ethyl ester

HRID 410365Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1-benzyl-1,3-dihydro-benzoimidazol-2-ylideneamine (247 mg, 1.10 mmol) in 2-butanone (40 ml) was added 3-(3-chloro-propoxy)-benzoic acid ethyl ester (0.40 g, 1.65 mmol) and KI (0.55 g, 3.32 mmol). The reaction was heated to 85° C. where it was maintained for 54 h. After this time, the mixture was cooled to rt and filtered. The filtrate was concentrated under reduced pressure and combined with the collected solid, washed with diethyl ether and petroleum ether and dried to provide 3-[3-(3-benzyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-propoxy]-benzoic acid ethyl ester (350 mg, 74%). HPLC-MS 430 [M+1]+.

Workup

temperaturewas maintained for 54 h
temperatureAfter this time, the mixture was cooled to rt
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
washwashed with diethyl ether and petroleum ether
customdried

Sources & evidence

ORD record: ord-fcce9034cf524fc1a188b15322c3a6b8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759520B2

Reaction notes

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