Ammonium Chloride → HCID 58203417, compound

HRID 2194811Notes

Reaction equation

HRID 2194811 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:13]2[N:14]([CH2:23][O:24][CH2:25][CH3:26])[C:15](=[O:22])[NH:16][C:17](=[O:21])[C:18]=2[CH2:19][CH3:20])C(=O)C)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C[O-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:13]2[N:14]([CH2:23][O:24][CH2:25][CH3:26])[C:15](=[O:22])[NH:16][C:17](=[O:21])[C:18]=2[CH2:19][CH3:20])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 58203538HCID 58203538, compound

Product 1

HCID 58203417HCID 58203417, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(3,5-dimethyl-phenyl)-N-(3-ethoxymethyl-5-ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acetamide (112) (93 mg, 0.26 mmol) in methanol (5 mL), was added sodium methoxide (73 mg, 1.35 mmol). After 4 hrs., the mixture was neutralized with excess NH4Cl and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 58 mg (70%) of a white solid. m.p. 175-176° C.; 1H-NMR (200 MHz, CDCl3) δ 0.93 (3H, t, J=7.5 Hz), 1.26 (3H, t, J=7.1 Hz), 2.19 (2H, q, J=7.5 Hz), 2.27 (6H, s), 3.70 (2H, q, J=7.1 Hz), 5.34 (2H, s), 6.42 (1H, s), 6.46 (2H, s), 6.65 (1H, s), 8.64 (1H, s); m/z (EI) 317 (M+).

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Sources & evidence

ORD record
ord-9a6c02f18dc34a83a636dfad4ddd38d8
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

Loading…