Pyridine → (3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl heptanoate

HRID 1751015Notes

Reaction equation

HRID 1751015 reaction equation
[C:1](Cl)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl:10][CH2:11][CH2:12][CH2:13][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([CH2:23][OH:24])[C:15]1=[O:25].N1C=CC=CC=1>ClCCl>[C:1]([O:24][CH2:23][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH2:13][CH2:12][CH2:11][Cl:10])[C:15]1=[O:25])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 17313Heptanoyl chlorideHCID 580468071-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-one

Product 1

HCID 58046749(3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl heptanoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heptanoyl chloride (0.64 mL, 4.15 mmol) was added dropwise at 0° C. to 1-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-one (1.00 g, 4.15 mmol) and pyridine (0.50 mL, 6.23 mmol) in dichloromethane (20 mL) and then allowed to warm to room temperature. The mixture was washed with water and brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (30% ethyl acetate/hexanes) to give product as an oil (1.35 g, 92%); NMR (DMSO-d6); δ0.80 (t, J=6.8 Hz, 3H); 1.15-1.19 (m, 6H); 1.46-1.49 (m, 2H); 2.08-2.12 (m, 2H); 2.30 (t, J=7.2 Hz, 2H); 3.67 (t, J=6.4 Hz, 2H); 3.97 (t, J=6.8 Hz, 2H); 5.88 (s, 2H); 7.10-7.16 (m, 2H); 7.24-7.29 (m, 2H); MS for C18H25ClN2O3 m/z 353 (M+H)+.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by PTLC (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cb94ec0ef40b438393403fbc1abe6827
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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