4-(Chloromethyl)-2-methyl-1,3-thiazole → HCID 23205613, compound

HRID 962487Notes

Reaction equation

HRID 962487 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][NH:7][CH2:8][CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1.Cl[CH2:32][C:33]1[N:34]=[C:35]([CH3:38])[S:36][CH:37]=1>C(O)C.O.O.C(O)C>[CH3:38][C:35]1[S:36][CH:37]=[C:33]([CH2:32][N:10]([CH2:11][C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[CH2:9][CH2:8][N:7]([CH2:32][C:33]2[N:34]=[C:35]([CH3:38])[S:36][CH:37]=2)[CH2:6][C:5]2[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:34]=1

Participants

6

Reactant 2

HCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 11133569HCID 11133569, compound

Product 1

HCID 23205613HCID 23205613, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
45 °C

Procedure

1.5 g N,N'-bis-(3,4,5-trimethoxybenzyl) ethylenediamine dichlorhydrate were solubilized in 30 ml of a 1:1 ethanol/water mixture. The pH of the solution was brought to 11 using a soda solution. A solution of 1.25 g 4-chloromethyl-2-methylthiazole in solution in 10 ml water were added all at once. The mixture was heated for 5 hours at 45° C., while maintaining the pH at between 10 and 11 by adding a soda solution. After cooling, the ethanol was evaporated under a vacuum and the mixture was acidified to a pH of 1 using concentrated HCl. Extraction was carried out using 3×25 ml dichloromethane, then the organic phase was dried and dry-evaporation effected. The oil obtained was taken up in 10 ml ethanol +0.5 ml concentrated HCl. The resultant precipitate was filtered and washed in ethylic ether. The solid was then recrystallized in 20 ml isopropanol containing 1% water. In this way, 600 mg of a white powder having a melting point of 190° C. was obtained, whose proton NMR spectrum (400 MHZ) and ultimate analysis matched the expected structure (existing as a dichlorhydrate).

Workup

  1. temperaturewhile maintaining the pH at between 10 and 11
  2. additionby adding a soda solution
  3. temperatureAfter cooling
  4. customthe ethanol was evaporated under a vacuum
  5. extractionExtraction
  6. customthe organic phase was dried
  7. customdry-evaporation
  8. customThe oil obtained
  9. filtrationThe resultant precipitate was filtered
  10. washwashed in ethylic ether
  11. customThe solid was then recrystallized in 20 ml isopropanol containing 1% water
  12. customwas obtained

Sources & evidence

ORD record
ord-4fcd4d24e7f74cf78acaef77298e1f4d
Source dataset
uspto-grants-1998_06
Patent number
US05760037

Reaction notes

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