Acetyl chloride → HCID 22493294, compound

HRID 1816288Notes

Reaction equation

HRID 1816288 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[N:20]([CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])=[O:25])=[N+]=[N-].C(Cl)(=O)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])=[CH:23][N:20]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11776TriphenylphosphineHCID 22493425HCID 22493425, compound

Product 1

HCID 22493294HCID 22493294, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Triphenylphosphine, polymer bound, (5.3 g, 3 mmol/g, Fluka Chimica, Buchs, Switzerland) was scurried in toluene (75 mL). A solution of 2-azido-2′-nitroacetophenone (2.18 g, 10.6 mmol) and acetyl chloride (0.848 g, 10.8 mmol) in toluene (25 mL) was added at room temperature, under a nitrogen atmosphere. The solution was stirred at room temperature for six hours, then filtered over celite. All volatiles were removed from the filtrate by evaporation under reduced pressure to yield 0.91 g of crude 2-methyl-5-(2-nitrophenyl)oxazole. Crude 2-methyl-5-(2-nitrophenyl)oxazole (0.905 g, 4.44 mmol) was reduced as in Example 64, and the product purified by silica chromatography to give 0.51 g of 5-(2-aminophenyl)-2-methyloxazole.

Workup

  1. filtrationfiltered over celite
  2. customAll volatiles were removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-03c30debab0e48efa9c5e98c48c3c4ce
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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