2-Methoxyethanol → HCID 22744124, compound

HRID 1860465Notes

Reaction equation

HRID 1860465 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[S:4][C:3]=1/[CH:8]=[CH:9]/[C:10](N(C)C)=O.Cl.OC[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH2:27])=[NH:26])=[CH:20][CH:19]=1.[OH-].[Na+].[O:30](CCO)[CH3:31]>>[CH3:7][C:5]1[S:4][C:3]([C:8]2[CH:9]=[CH:10][N:26]=[C:25]([NH:24][C:21]3[CH:22]=[C:23]([CH2:31][OH:30])[CH:18]=[CH:19][CH:20]=3)[N:27]=2)=[C:2]([CH3:1])[N:6]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneHCID 178479377HCID 178479377, compound

Product 1

HCID 22744124HCID 22744124, compoundYield 70%

Procedure

A mixture of 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone (10 mmol, 2.1 g) in 2-methoxylethanol was treated with N-(4-hydroxymethyl-phenyl)-guanidine hydrochloride (1.65 g) in the presence of NaOH (400 mg). The reaction mixture was allowed to reflux for 20 h. After concentration, the precipitates were filtered and washed with EtOAc/MeOH several times. Recrystallisation from MeOH/EtOAc afforded the title compound (2.17 g, 70%). 1H-NMR (300 MHz, d6-DMSO) δ 3.00 (s, 3H, CH3), 3.02 (s, 3H, CH3), 4.86 (s, 2H, CH2), 7.30 (m, 1H, Ph-H), 7.44 (d, 1H, J=6.1 Hz, pyrimidinyl-H), 7.61 (m, 1H, Ph-H), 8.01 (m, 1H, Ph-H), 8.13 (s, 1H, Ph-H), 8.88 (d, 1H, J=6.1 Hz, pyrimidinyl-H).

Workup

  1. temperatureto reflux for 20 h
  2. concentrationAfter concentration
  3. filtrationthe precipitates were filtered
  4. washwashed with EtOAc/MeOH several times
  5. customRecrystallisation from MeOH/EtOAc

Sources & evidence

ORD record
ord-b310e4afb3de4fd198d7d5b80fa4ff73
Source dataset
uspto-grants-2003_03
Patent number
US06531479B2

Reaction notes

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