Sodium Nitrite → HCID 22644641, compound

HRID 2414344Notes

Reaction equation

HRID 2414344 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:7](C(C)(C)C)=[C:8]([CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][O:23][C:22]2=[O:31])[CH2:17][CH2:16]1)[C:9]([O-:11])=[O:10]>O.C(#N)C.CN(C)C=O.S([O-])([O-])(=O)=O.[Fe+2]>[O:31]=[C:22]1[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:21]1[CH:18]1[CH2:17][CH2:16][N:15]([C:14]2[CH:6]=[CH:7][C:8]([C:9]([O:11][C:8]([CH3:12])([CH3:9])[CH3:7])=[O:10])=[CH:12][CH:13]=2)[CH2:20][CH2:19]1

Participants

7

Reactant 2

HCID 23668193Sodium NitriteHCID 131724636HCID 131724636, compound

Product 1

HCID 22644641HCID 22644641, compound

Reagents, catalysts & solvents 4

HCID 24393Ferrous SulfateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of sodium nitrite (0.11 g) in water (1 ml) was added to a stirred solution of the product from example 159 step (ii) (0.456 g) in acetonitrile (10 ml) at room temperature. After 1 h a solution of iron sulphate (0.3 g) in N,N-dimethylformamide (20 ml) was added and the mixture stirred for a further 30 min. The mixture was partitioned between ethyl acetate and water, the organics dried and evaporated under reduced pressure. Purification was by chromatography eluting with 20% ethyl acetate/isohexane. Yield 0.29 g as an oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organics dried
  3. customevaporated under reduced pressure
  4. customPurification
  5. washeluting with 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-7f621a1a277b4a11b96e297c0380f560
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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