Chlorosuccinimide → ethyl 4-chloro-5-propyl-1H-imidazole-2-carboxylate

HRID 43492Notes

Reaction equation

[CH2:1]([C:4]1[NH:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:5]=1)[CH2:2][CH3:3].C1C(=O)N([Cl:21])C(=O)C1>>[Cl:21][C:5]1[N:6]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:8][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 14990234ethyl 5-propyl-1H-imidazole-2-carboxylate

Product 1

HCID 67548193ethyl 4-chloro-5-propyl-1H-imidazole-2-carboxylateYield 73.5%

Procedure

The same operation as in Example (1c) was performed using ethyl 5-propyl-1H-imidazole-2-carboxylate obtained in Example (46b) (1.01 g, 5.54 mmol) and NCS (0.74 g, 5.50 mmol), to obtain 876 mg of the title compound as a white solid (73%).

Sources & evidence

ORD record: ord-b4e4daa318bf445eb089adbc4eb6aea1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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