1,2-Dichloroethane → HCID 18956345, compound

HRID 2379895Notes

Reaction equation

HRID 2379895 reaction equation
[NH2:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.C(N(CC)CC)C.BrCC[CH2:21][CH2:22][C:23](Cl)=[O:24].[CH2:26]([Cl:29])[CH2:27]Cl>>[Cl:29][CH2:26][CH2:27][CH2:21][CH2:22][C:23]([NH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1)=[O:24]

Participants

5

Reactant 4

HCID 111,2-Dichloroethane2×HCID 8471TriethylamineHCID 136242-AminobenzimidazoleHCID 5211735-Bromovaleryl chloride

Product 1

HCID 18956345HCID 18956345, compound

Procedure

Part A. A solution of 2-amino-1H-benzimidazole (5.00 g, 57.5 mmol) and triethylamine (7.50 mL, 53.8 mmol) in ethylene dichloride (150 mL) was treated with a solution of 5-bromovaleryl chloride (5.00 mL, 37.6 mmol) in ethylene dichloride (50 mL) with stirring, for 20 hours at ambient temperature. The solution was washed with water (2×200 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to afford a solid. The solid was recrystallized from methanolacetonitrile to afford pure 5-chloro-N-(1H-benzimidazol-2-yl)-pentanamide, m.p. 161°-163° C. (2.98 g, 11.8 mmol). 1H NMR (d6 -DMSO): 12.14 (1H, br s); 11.56 (1H, br s); 7.44 (2H, dd, J=5.9, 3.0 Hz); 7.08 (2H, dd, J=5.8, 2.9 Hz); 3.58 (2H, t, J=6.6 Hz); 2.49 (2H, t, J=6.9 Hz); 1.96-1.71 (4H, m). Successive crops of solid from the mother liquor proved to be 5-bromo-N-(1H-benzimidazol-2-yl)-pentanamide (2.85 g, 9.62 mmol; total yield of products 58%).

Workup

  1. washThe solution was washed with water (2×200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a solid
  6. customThe solid was recrystallized from methanolacetonitrile

Sources & evidence

ORD record
ord-5e05e9e6837046ba810c8ae8af8bf9d7
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

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