Chlorosuccinimide → HCID 19815317, compound

HRID 653869Notes

Reaction equation

HRID 653869 reaction equation
[CH2:1]([C:8]1[NH:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl:15]N1C(=O)CCC1=O>>[Cl:15][C:11]1[N:12]=[C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[NH:9][C:10]=1[CH2:13][OH:14]

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 19815382HCID 19815382, compound

Product 1

HCID 19815317HCID 19815317, compoundYield 48.4%

Procedure

To a solution of 2-heptyl-5-(hydroxymethyl)-imidazole (10.0 g, 51 mmol) in EtOH1,4-dioxane (1:1; 600 mL) was added N-chlorosuccinimide (7.9 g, 59 mmol). After being stirred for 1 hour at room temperature the solvents were removed on a rotary evaporator an the solid residue was partitioned between ethyl acetate and water (300 mL each). The organic phase was washed with water (150 mL), dried (MgSO4), filtered and concentrated to afford 12.4 g crude product. Recrystallization (1:1 EtOAc/hexane, 60 mL) gave 5.7 g (45%) of white crystals; m.p. 134°-140°. NMR (200 MHz, CDCl3 /CD3OD) δ 4.50 (s, 2H); 4.00-3.80 (br s, 2H); 2.65 (t 2H, 5Hz); 1.80-1.60 (m, 2H); 1.40-1.20 (m, 8); 0.90-0.80 (m, 3H). Mass Spec. 230.

Workup

  1. customwere removed on a rotary evaporator an the solid residue
  2. customwas partitioned between ethyl acetate and water (300 mL each)
  3. washThe organic phase was washed with water (150 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford 12.4 g crude product
  8. customRecrystallization (1:1 EtOAc/hexane, 60 mL)

Sources & evidence

ORD record
ord-fb7df1c68d9b4593be2a9e6f69b918dc
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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