2-Methoxyethanol → HCID 22744124, compound

HRID 47209Notes

Reaction equation

HRID 47209 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) δ3.00 (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-bccebd2fbcbe4f479c16c3a745c226fc
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Reaction notes

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