Hydrochloric Acid → HCID 15907991, compound

HRID 651477Notes

Reaction equation

HRID 651477 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[S:9][CH:10]=1)C.[OH-].[Na+].O1CCCC1.Cl>[Cl-].[Na+].O.C(OCC)(=O)C>[O:30]=[C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:31])=[O:3])[N:7]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86751620HCID 86751620, compound

Product 1

HCID 15907991HCID 15907991, compoundYield 39.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl-2-[((Z)-1-oxo-9-octadecenyl)amino]-4-thiazoleacetate (4 g, 8.89 mmol), sodium hydroxide (0.79 g, 19.8 mmol) and tetrahydrofuran (50 mL) were combined and cooled in an ice bath under N2 atmosphere. Enough distilled water was added to the mixture to dissolve the hydroxide and provide a homogeneous solution. The reaction was kept at 0° C. for 2 h, then allowed to warm to room temperature and stirred overnight. Aqueous 10% HCl solution was added to the mixture, and stirring continued for 1 h. Ethyl acetate and saturated aqueous brine solution were added to the mixture, and the organic phase was separated and dried over MgSO4. After filtration and concentration the crude dark amber oil was treated with ether, stirred for 0.5 h and the product was collected on a Buchner funnel and air dried to give 1.5 g of the title compound as a white solid, mp 106-108.5° C.

Workup

  1. temperaturecooled in an ice bath under N2 atmosphere
  2. distillationEnough distilled water
  3. additionwas added to the mixture
  4. dissolutionto dissolve the hydroxide
  5. customprovide a homogeneous solution
  6. stirringstirring
  7. waitcontinued for 1 h
  8. customthe organic phase was separated
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration and concentration the crude dark amber oil
  11. additionwas treated with ether
  12. stirringstirred for 0.5 h
  13. customthe product was collected on a Buchner funnel and air
  14. customdried

Sources & evidence

ORD record
ord-75d644d02dda41dd949ceb7923e11265
Source dataset
uspto-grants-2001_08
Patent number
US06281234B1

Reaction notes

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