Benzoyl chloride → HCID 20290849, compound

HRID 1413807Notes

Reaction equation

HRID 1413807 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.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.CCOCC>[C:32]([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:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 451690HCID 451690, compound

Product 1

HCID 20290849HCID 20290849, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4,5-bis(4-methoxyphenyl)-2-nitroimidazole (3 g, 9.2 mmole) and triethylamine (3.9 ml., 27.6 mmole) in 30 ml. THF at 0° C. under N2 was dropwise added a solution of benzoyl chloride (1.2 ml., 10.1 mmole) in 5 ml THF. The reaction mixture was stirred for 8 hours at 0° C. and then left in the refrigerator overnight. The reaction was then diluted with 30 ml ether and filtered. The filtrate was concentrated on a rotary evaporator and chromatographed on Florisil. Recrystallization from methylcyclohexane gave 1.89 g of 1-benzoyl-4,5-bis(4-methoxyphenyl)-2-nitroimidazole, mp. 161°-163° C.

Workup

  1. waitleft in the refrigerator overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated on a rotary evaporator
  4. customchromatographed on Florisil
  5. customRecrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-fda3a75af9cb49638d6d6d431a95afb6
Source dataset
uspto-grants-1981_02
Patent number
US04251535

Reaction notes

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