Acetyl chloride → HCID 20290850, compound

HRID 1413808Notes

Reaction equation

HRID 1413808 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([N+:22]([O-:24])=[O:23])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.C1C[O:35][CH2:34][CH2:33]1.C(Cl)(=O)C>C(OCC)(=O)C>[C:34]([N:10]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:12]=[C:11]1[N+:22]([O-:24])=[O:23])(=[O:35])[CH3:33]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 451690HCID 451690, compound

Product 1

HCID 20290850HCID 20290850, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,5-bis(4-methoxyphenyl)-2-nitroimidazole (3.0 g, 9.22 mmole) and triethylamine (7 ml., 51 mmole) in 30 ml. THF at 0° C. under N2 was dropwise added a solution of acetyl chloride (1.3 ml., 18.4 mmole) in 5 ml. THF. After 2 hours at 0° C., the reaction mixture was diluted with ethyl acetate washed with 1N HCl, saturated aqueous NaHCO3 and brine, dried and concentrated on a rotary evaporator. Crystallization from ether gave approximately 600 mg. of starting material. HPLC of the mother liquor and crystallization from ether gave 1-acetyl 4,5-bis(4-methoxyphenyl)-2-nitroimidazole, mp. 146°-151° C. H-NMR indicates purity >95%. H-NMR: 2.41δ (s, 3H), 3.8δ (s, 3H), 6.73-7.56 δ(2AB quartets, J=9Hz, 8H).

Workup

  1. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated on a rotary evaporator
  4. customCrystallization from ether
  5. customgave approximately 600 mg
  6. customHPLC of the mother liquor and crystallization from ether

Sources & evidence

ORD record
ord-8f9124bce5bf4f5b978bdfc8e9351428
Source dataset
uspto-grants-1981_02
Patent number
US04251535

Reaction notes

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