HCID 66652237, compound → 6-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 1751047Notes

Reaction equation

HRID 1751047 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6](C(OC(C)(C)C)=O)[C:7](=[O:13])[N:8]([CH2:9][CH2:10][CH2:11][Cl:12])[C:4]=2[CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7](=[O:13])[N:8]([CH2:9][CH2:10][CH2:11][Cl:12])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 66652237HCID 66652237, compound

Product 1

HCID 203855876-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneYield 135.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 5-chloro-3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate (528 mg, 1.53 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated and dried in vacuo to afford the hydrogen chloride salt of the title compound as a cream powder (507 mg, quant); 1H NMR (400 MHz, DMSO-d6): δ 2.03-2.12 (m, 2H); 3.63-3.72 (m, 2H); 3.90 (t, 2H, J=7.2 and 6.8 Hz); 7.00 (d, 1H, J=2 Hz); 7.02 (dd, 1H, J=2 Hz); 7.15 (d, 1H, J=8 Hz); MS for C10H10Cl2N2O m/z 244.93 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-7f4522b77595431dac8b54e54c20896a
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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