Hydrochloric Acid → HCID 59238221, compound

HRID 1359917Notes

Reaction equation

HRID 1359917 reaction equation
N(OC(C)(C)C)=O.[C:8]([Cu])#[N:9].[Br:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15](N)=[C:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=2)[CH:13]=1.Cl>CS(C)=O>[Br:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([C:8]#[N:9])=[C:14]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 59238226HCID 59238226, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59238221HCID 59238221, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

Tert-butyl nitrite (1.1 mL) is added to a 60° C.-warm solution of CuCN (0.36 g) in DMSO (3 mL). Then, a solution of 4-bromo-2-(4-ethyl-benzyl)-5-methoxy-phenylamine (1.0 g) in DMSO is added dropwise and the resulting solution is stirred for 1 h at 60° C. After cooling to room temperature, the solution is acidified by the addition of 5 N aqueous hydrochloric acid. The resulting mixture is extracted with ethyl acetate and the combined extracts are dried (Na2SO4). After removal of the solvent, the residue is purified by chromatography on silica gel (cyclohexane/dichloromethane 3:1->1:3) to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. dry with materialthe combined extracts are dried (Na2SO4)
  4. customAfter removal of the solvent
  5. customthe residue is purified by chromatography on silica gel (cyclohexane/dichloromethane 3:1->1:3)

Sources & evidence

ORD record
ord-bb8aa80268f8444b9b8e40949a7c6025
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

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