Isoamyl Nitrite → HCID 54317118, compound

HRID 1417563Notes

Reaction equation

HRID 1417563 reaction equation
N[C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:17])[CH3:16])=[C:10]([Br:18])[CH:9]=2)=[C:5]([CH3:7])[N:6]=1.N(OCCC(C)C)=O>C1COCC1>[Br:18][C:10]1[CH:9]=[C:8]([C:4]2[S:3][CH:2]=[N:6][C:5]=2[CH3:7])[CH:13]=[CH:12][C:11]=1[O:14][CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 54334081HCID 54334081, compound

Product 1

HCID 54317118HCID 54317118, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 118 mg (0.361 mmol) of 2-amino-5-(3-bromo-4-isopropoxyphenyl)-4-methylthiazole (from Example 230, Step B) in 3.6 mL of THF was added to a solution of 0.107 mL (93 mg, 0.80 mmol) of isoamyl nitrite in 2.4 mL of THF. The resulting solution was refluxed for 1 h. The cooled mixture was partitioned between 25 mL of dichloromethane and 10 mL of water, and the aqueous layer was extracted with 2×25 mL of dichloromethane. The combined organic layers were dried over sodium sulfate, decanted, and evaporated. The crude product was purified by flach column chromatography, eluting with 5% ethyl acetate in hexane, to give 51 mg of the title compound as a yellow solid. Mass spectrum (NH3/CI): m/z=312 (M+1).

Workup

  1. temperatureThe resulting solution was refluxed for 1 h
  2. customThe cooled mixture was partitioned between 25 mL of dichloromethane and 10 mL of water
  3. extractionthe aqueous layer was extracted with 2×25 mL of dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customdecanted
  6. customevaporated
  7. customThe crude product was purified by flach column chromatography
  8. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1778254a8fef41a68f1d031c1aab5eea
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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