Sodium Azide → HCID 178426099, compound

HRID 1472777Notes

Reaction equation

HRID 1472777 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]#[N:22])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH3:20])=[C:4]([CH3:23])[CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>[Br-].[Zn+2].[Br-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[NH:26][N:25]=[N:24][N:22]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[CH3:20])=[C:4]([CH3:23])[CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 68294348HCID 68294348, compound

Product 1

HCID 178426099HCID 178426099, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Conditions

Temperature
150 °C

Procedure

A round-bottomed flask was charged with 4,5-bis(4-chloro-2-methylphenyl)thiazole-2-carbonitrile (150 mg, 0.42 mmol), zinc bromide (189 mg, 0.84 mmol) and sodium azide (45.5 mg, 0.84 mmol). After degassed, DMF (3 mL) was added. The reaction mixture was heated to 150° C. overnight. After cooled to rt, the reaction was quenched with 30 mL of 0.1 N aqueous HCl, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:EtOAc:AcOH=30:10:1). 120 mg of product was obtained as a white solid, 1H NMR (DMSO, 500 MHz) δ 7.93 (d, J=8.41 Hz, 1H), 7.57 (d, J=1.90 Hz, 1H), 7.49-7.44 (m, 2H), 7.33-7.28 (m, 2H), 2.63 (s, 3H), 2.18 (s, 3H); 13C NMR (DMSO, 125 MHz) δ 166.07, 153.61, 139.50, 138.74, 134.92, 133.48, 132.53, 131.87, 131.42, 130.27, 129.98, 126.64, 125.67, 21.13, 19.51.

Workup

  1. customAfter degassed
  2. additionDMF (3 mL) was added
  3. temperatureAfter cooled to rt
  4. customthe reaction was quenched with 30 mL of 0.1 N aqueous HCl
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (hexane:EtOAc:AcOH=30:10:1)

Sources & evidence

ORD record
ord-083e13f55f924029887188bc3e100cde
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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