1,1'-Carbonyldiimidazole → HCID 19351177, compound

HRID 1636377Notes

Reaction equation

HRID 1636377 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[CH2:9][NH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:35][OH:36]>C1COCC1>[C:1]1(/[CH:7]=[CH:8]/[CH2:9][NH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:35][OH:36])=[O:18])=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 19351110HCID 19351110, compound

Product 1

HCID 19351177HCID 19351177, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step A (0.7 g, 2.3 mmoles) was dissolved in 8 ml of anhydrous THF and added at 0° C. with CDI (0.46 g, 2.8 mmoles). The mixture was stirred at room temperature overnight, then hydroxylamine hydrochloride (0.2 g, 2.3 mmoles) was added thereto and stirring was continued at room temperature for a further 60 hours. The formed precipitate was filtered and suspended in 1N HCl, then stirred overnight. Upon filtration and drying under vacuum, 400 mg of the title compound were obtained (55.6% yield); m.p.=194-195° C.

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for a further 60 hours
  3. filtrationThe formed precipitate was filtered
  4. stirringstirred overnight
  5. filtrationUpon filtration
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-1c8edf96b12b45b48c80afcaa0c567b5
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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