Hydrochloric Acid → N-butyl-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-methyl-5-oxo-1-pyrazolidinecarboxamide hydrochloride

HRID 1612944Notes

Reaction equation

HRID 1612944 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[N:19]([CH3:20])[NH:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25].[ClH:29]>C(Cl)(Cl)Cl.N#N.CCOCC>[ClH:29].[CH2:22]([NH:26][C:27]([N:18]1[C:17](=[O:21])[CH2:16][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[N:19]1[CH3:20])=[O:28])[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 197927655-[3-(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone

Product 1

HCID 19792803N-butyl-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-methyl-5-oxo-1-pyrazolidinecarboxamide hydrochlorideYield 56%

Reagents, catalysts & solvents 3

HCID 947NitrogenSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

5-[3-(cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone (2.06 mmol, 0.600 g) is dissolved in dry chloroform (10 mL) in a N2 atmosphere. To this is added dropwise at room temperature butyl isocyanate (5.15 mmol; 0.583 mL) neat. The sample is heated to reflux for 4 hours at which time TLC shows no starting material. The sample is evaporated to yield a clear oil which is dissolved in ether. To this solution is added ethanolic HCl and the sample is stirred for 15 minutes and evaporated in vacuo to afford a solid which is recrystallized from chloroform and hexane to give the title compound as a white solid (0.495 mg; 56%) m.p.: 115°-122° C. (dec) 1H NMR (DMSO-d6, 400 MHz) δ8.3 (s, 1H); 7.91 (t, 3H, J=5.7 Hz); 6.95 (d, 1H, J=1.3 Hz); 6.89 (d, 1H, J=8.3 Hz); 6.81 (dd, 1H, J=8.3, 1.6 Hz); 4.68 (m, 1H); 4.35 (d, 1H, J=5.6 Hz); 3.69 (s, 3H); 3.15 (m, 2H); 2.73 (s, 3H); 1.84 (m, 2H); 1.68 (m, 3H); 1.54 (m, 2H); 1.40 (m, 2H); 1.23 (m, 3H); 0.85 (t, 2H, J=7.3 Hz). IR (KBr, cm-1) 1760

Workup

  1. temperatureThe sample is heated
  2. temperatureto reflux for 4 hours at which time TLC
  3. customThe sample is evaporated
  4. customto yield a clear oil which
  5. customevaporated in vacuo
  6. customto afford a solid which
  7. customis recrystallized from chloroform and hexane

Sources & evidence

ORD record
ord-6e9deaa784974ec09b5f977740b782f4
Source dataset
uspto-grants-1993_03
Patent number
US05191084

Reaction notes

Loading…