Water → HCID 20276433, compound

HRID 370554Notes

Reaction equation

HRID 370554 reaction equation
[N+:1]([O-:27])([O:3][CH2:4][C:5]1[N:9](C(=O)C)[C:8](=[O:13])[N:7]([C:14](=[O:16])[CH3:15])[C:6]=1[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:2].N1CCCCC1.O>C(OCC)C.C(OCC)(=O)C>[N+:1]([O-:27])([O:3][CH2:4][C:5]1[NH:9][C:8](=[O:13])[N:7]([C:14](=[O:16])[CH3:15])[C:6]=1[C:17](=[O:26])[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 13477227HCID 13477227, compound

Product 1

HCID 20276433HCID 20276433, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a cold solution (10° C.) of 1.9 g of [1,3-diacetyl-4-(4-methoxybenzoyl)-1,3-dihydro-2-oxo-2H-imidazol-5-yl]-methyl nitrate in 30 ml of ethyl ether and 20 ml of ethyl acetate there is added a solution of 470 mg of piperidine in 10 ml of ethyl ether and the solution is stirred at 25° C. for 30 minutes. Water (30 ml) is added and the precipitate which forms is separated and recrystallized twice from ethyl acetate to give [1-acetyl-1,3-dihydro-5-(4-methoxybenzoyl)-2-oxo-2H-imidazol-4-yl]methyl nitrate melting at about 165°-166° C. with decomposition.

Workup

  1. customthe precipitate which forms is separated
  2. customrecrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-6025e5c3294d443195922ad00592821d
Source dataset
uspto-grants-1985_07
Patent number
US04526981

Reaction notes

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