Hydrochloric Acid → N-cyclohexyl-N'-[3-[4-nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)-methyl]phenoxy] propyl]urea

HRID 1614172Notes

Reaction equation

HRID 1614172 reaction equation
[Na].[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH:5](P(OCC)(=O)OCC)[NH:4]1.[CH:17]1([NH:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[C:33]([CH:40]=O)[CH:32]=2)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>CCO>[CH:17]1([NH:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[C:33]([CH:40]=[C:5]3[NH:4][C:3](=[O:2])[NH:7][C:6]3=[O:8])[CH:32]=2)=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3516088Diethyl 5-hydantoylphosphonateHCID 5360545SodiumHCID 19773195N-Cyclohexyl-N'-[3-(3-formyl-4-nitrophenoxy)propyl]urea

Product 1

HCID 53651698N-cyclohexyl-N'-[3-[4-nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)-methyl]phenoxy] propyl]ureaYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.50 g, 20 mg atom) was dissolved in absolute EtOH (100 mL), diethyl 2,4-dioxoimidazolidine-5-phosphonate (4.70 g, 20 mmol) added and the mixture stirred at room temperature for about 15 minutes. N-Cyclohexyl-N'-[3-(3-formyl-4-nitrophenoxy)propyl]urea (5.33 g, 15 mmol) in EtOH (75 mL) was added and the mixture stirred for about 1 hour. The solution was acidifed with 2N HCl solution, concentrated to ca. 75 mL and diluted with water. After stirring overnight, a pale yellow solid was filtered off and dried in air to give N-cyclohexyl-N'-[3-[4-nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)-methyl]phenoxy] propyl]urea (6.50 g, 99 %). A 1.00 g sample was recrystallized from aqueous acetonitrile to give 0.79 g as a 5:1 (Z) to (E) mixture, mp 132°-138° C. IR (KBr) 1760, 1725, 1650, 1570, 1500, 1375, 1340, 1290, 1250 cm-1 ; 1 H NMR (DMSO-d6) δ 1.00 to 2.00 (10H, m, CH2 of cyclohexyl ring), 3.30 (2H, quintet, J=6 Hz, CO.NH.CH2), 3.35 (1H, m, N-CH), 4.11 (0.32H, t, J=6Hz, OCH2 of (Z) isomer), 4.20 (1.67H, t, J=6 Hz, OCH2 of (E) isomer), 6.62 (0.16H, s, olefinic H of (Z) isomer), 6.74 (0.84H, s, olefinic H of (E) isomer), 7.05 to 7.20 (2H, m, aryl H), 8.15 (1H, 2×d, aryl H ortho to NO2); MS m/Z 432 (MH+).

Workup

  1. stirringthe mixture stirred for about 1 hour
  2. concentrationconcentrated to ca. 75 mL
  3. additiondiluted with water
  4. stirringAfter stirring overnight
  5. filtrationa pale yellow solid was filtered off
  6. customdried in air

Sources & evidence

ORD record
ord-b551f854b0c640e4ac448c91b435222e
Source dataset
uspto-grants-1993_03
Patent number
US05196428

Reaction notes

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