Acetic Anhydride → HCID 117690902, compound

HRID 2174933Notes

Reaction equation

HRID 2174933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[CH2:13][CH3:14].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].C1OCCOCCOCCOCCOCCOC1.[N:45](OCCC(C)C)=O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH2:13][CH3:14])=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([C:9](=[O:11])[CH3:10])[N:45]=[CH:12]2

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 89601742HCID 89601742, compound

Product 1

HCID 117690902HCID 117690902, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.72 g of the acetamide prepared in Example 212b in 31.5 ml chloroform were added 4.1 ml of acetic anhydride and 2.85 g of potassium acetate, and 192 mg of 18-crown-6 and 3.4 g of isopentyl nitrite were then added dropwise. The reaction mixture was heated for 20 hours under reflux and after cooling diluted with 200 ml ethyl acetate. The organic phase was washed with 20 ml sodium carbonate solution and once with saturated sodium chloride solution. After drying over sodium sulphate and filtration, this was concentrated in vacuo and the crude product thus obtained purified by column chromatography on silica gel with hexane/0-50% ethyl acetate. Yield: 3.78 g of the title compound.

Workup

  1. additionwere then added dropwise
  2. temperatureThe reaction mixture was heated for 20 hours
  3. temperatureunder reflux
  4. temperatureafter cooling
  5. washThe organic phase was washed with 20 ml sodium carbonate solution and once with saturated sodium chloride solution
  6. dry with materialAfter drying over sodium sulphate and filtration
  7. concentrationthis was concentrated in vacuo

Sources & evidence

ORD record
ord-9cc71bf0d98d4c7db505f2ac7a07a0a1
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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