Triethylamine → HCID 178495980, compound

HRID 1734023Notes

Reaction equation

HRID 1734023 reaction equation
C([O:4][CH2:5][C:6]([Cl:8])=[O:7])(=O)C.Cl.Cl.[NH2:11][CH2:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]=[C:21]([N:24]=[C:25]([NH2:31])[NH:26][CH2:27][CH2:28][O:29][CH3:30])[S:22][CH:23]=2)[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C>ClCCl>[ClH:8].[NH2:31][C:25](=[N:24][C:21]1[S:22][CH:23]=[C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][NH:11][C:6](=[O:7])[CH2:5][OH:4])[CH:14]=2)[N:20]=1)[NH:26][CH2:27][CH2:28][O:29][CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 178495975HCID 178495975, compound

Product 1

HCID 178495980HCID 178495980, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetoxyacetyl chloride (1.08 g) in dichloromethane (10 ml) was added slowly to a suspension of 4-(3-aminomethylphenyl)-2-[[(amino)(2-methoxyethyl-amino)methylene]amino] thiazole dihydrochloride (2.5 g) and triethylamine (1.60 g) in dichloromethane (40 ml) with cooling on an ice bath. The mixture was stirred at room temperature for 1 day. The solvent was removed under reduced pressure. The residue was suspended in water (100 ml). The mixture was alkalified with an aqueous potassium carbonate solution and then extracted with a mixture of ethyl acetate (250 ml) and tetrahydrofuran (50 ml). The extract was dried with magnesium sulfate and then was evaporated in vacuo. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (20:1). The solvent was removed under reduced pressure. The residue was dissolved in methanolic ammonia (50 ml). The mixture was stirred with cooling on an ice-water bath for 1 hour. The solvent was removed under reduced pressure. The residue was dissolved in ethanol (50 ml) and 4N- dioxane solution of hydrogen chloride (10 ml) was added to the mixture. The mixture was stirred at room temperature for 4 hours. The resulting precipitate was collected by filtration. Recrystallization from ethanol afforded 2-[[(amino)(2-methoxyethylamino)methylene]amino]-4-(3-hydroxyacetamidomethylphenyl)thiazole hydrochloride (0.57 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted with a mixture of ethyl acetate (250 ml) and tetrahydrofuran (50 ml)
  4. dry with materialThe extract was dried with magnesium sulfate
  5. customwas evaporated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with a mixture of chloroform and methanol (20:1)
  8. customThe solvent was removed under reduced pressure
  9. dissolutionThe residue was dissolved in methanolic ammonia (50 ml)
  10. stirringThe mixture was stirred
  11. temperaturewith cooling on an ice-water bath for 1 hour
  12. customThe solvent was removed under reduced pressure
  13. dissolutionThe residue was dissolved in ethanol (50 ml)
  14. addition4N- dioxane solution of hydrogen chloride (10 ml) was added to the mixture
  15. stirringThe mixture was stirred at room temperature for 4 hours
  16. filtrationThe resulting precipitate was collected by filtration
  17. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f7952741fb984d8baa65ea77fbe1cd48
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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