Chlorosuccinimide → HCID 19815317, compound

HRID 465776Notes

Reaction equation

HRID 465776 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>CCO.O1CCOCC1>[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

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 19815382HCID 19815382, compound

Product 1

HCID 19815317HCID 19815317, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 22560076Dioxan ethanolSolvent

Procedure

To a solution of 2-heptyl-5-(hydroxymethyl)-imidazole (10.0 g, 51 mmol) in EtOH/1,4-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 and 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) δ4.50 (s, 2H); 4.00-3.80 (br s, 2H); 2.65 (t, 2H, 5 Hz); 1.80-1.60 (m, 2H); 1.40-1.20 (m, 8H); 0.90-0.80 (m, 3H). Mass Spec. 230.

Workup

  1. customwere removed on a rotary evaporator
  2. customthe solid residue was 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-21ed9b69bb994531af51e10a5cf0c974
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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