1,1'-Carbonyldiimidazole → HCID 19759914, compound

HRID 1586860Notes

Reaction equation

HRID 1586860 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([NH:17][S:18]([C:21]1[S:25][C:24]2[S:26](=[O:33])(=[O:32])[CH:27]([C:29]([OH:31])=[O:30])[CH2:28][C:23]=2[CH:22]=1)(=[O:20])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(Cl)CCC>[C:13]([NH:17][S:18]([C:21]1[S:25][C:24]2[S:26](=[O:32])(=[O:33])[CH:27]([C:29]([O:31][CH3:1])=[O:30])[CH2:28][C:23]=2[CH:22]=1)(=[O:20])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19759866HCID 19759866, compound

Product 1

HCID 19759914HCID 19759914, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Procedure

Carbonyldiimidazole (5.3 g, 32.7 mmol) was added at room temperature to a stirred solution of product from Step A (7.7 g, 21.8 mmol) in dry, degassed DMF under an N2 atmosphere. After 1 h, methanol (150 mL) was added and the reaction stirred for 30 min. The solvents were removed under high vacuum, and the residue taken up in ethyl acetate. This solution was extracted with water and saturated brine, dried over MgSO4, filtered, and the filtrate evaporated to dryness to give a foam. This foam was treated with n-butyl-chloride and the resulting solid filtered and dried in the air to give the title compound (5.7, 74%). 1H NMR (300 MHz,DMSO-d6) 1.20(s,9H), 3.53(d,2H), 3.80(s,3H), 5.30(t,1H), 7.60(s,1H, 8.20(s,1H,exch.).

Workup

  1. customin dry
  2. customdegassed DMF under an N2 atmosphere
  3. additionmethanol (150 mL) was added
  4. customThe solvents were removed under high vacuum
  5. extractionThis solution was extracted with water and saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness
  9. customto give a foam
  10. filtrationthe resulting solid filtered
  11. customdried in the air

Sources & evidence

ORD record
ord-7f9b02a807364d0cb10b8ffa5e4b05bb
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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