HCID 178418546, compound → HCID 178439233, compound

HRID 276302Notes

Reaction equation

HRID 276302 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[S:13][CH2:12][C:11]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:10]2)=[C:4]([CH2:18][CH2:19][CH3:20])[CH:3]=1.[C:21]([Cu])#[N:22]>CN(C=O)C>[C:21]([C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[S:13][CH2:12][C:11]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:10]2)=[C:4]([CH2:18][CH2:19][CH3:20])[CH:3]=1)#[N:22]

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178439353HCID 178439353, compound

Product 1

HCID 178439233HCID 178439233, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Iodo-2-n-propylaniline was converted into 4-iodo-2-n-propylphenyl isothiocyanate in a manner analogous to Method A2b. Concurrently, 1-amino-1-(hydroxymethyl)cyclopentane was converted to the chloromethyl analogue, then reacted with the isothiocyanate in a manner analogous to Method C2a to give 2-(4-iodo-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane. A slurry of 2-(4-iodo-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane (0.54 g, 1.35 mmol) and CuCN (0.24 g, 2.70 mmol) in DMF (4 mL) was heated at 140° C. overnight. The resulting mixture was cooled to room temp, concentrated under reduced pressure and purified by flash chromatography (10% EtOAc/hex) to give 2-(4-cyano-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane as a white solid (0.26 g, 65%): TLC (30% EtOAc/hex) Rf0.37.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography (10% EtOAc/hex)

Sources & evidence

ORD record
ord-15377e7a7be7450085c5cf8eb0105802
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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