Ethyl Acetate → HCID 86618621, compound

HRID 1436461Notes

Reaction equation

HRID 1436461 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][C:14](=O)[C:15](OCC)=[O:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([NH:13][CH2:14][CH2:15][OH:16])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 1850316Acetic acid, ((4-(4-chlorophenyl)-2-thiazolyl)amino)oxo-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 86618621HCID 86618621, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl {[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}(oxo)acetate (2.50 g, 8.04 mmol), prepared in the previous step, in dry tetrahydrofuran (25 mL) was added, under nitrogen, to a stirred suspension of lithium aluminum hydride (0.92 g, 24 mmol) in dry tetrahydrofuran (25 mL). After the addition was complete, the mixture was stirred for an additional 1 h. Ethyl acetate (4.8 mL) was added dropwise, followed by water (0.92 mL), 4N NaOH (0.92 mL) and water (2.8 mL). The mixture was then filtered and evaporated to afford 2-{[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino}ethanol (1.12 g, 55%) which was used without further purification. HRMS: calcd for C11H11ClN2OS [M+H+], 255.03534; found (ESI+, [M+H]+), 255.03505.

Workup

  1. additionAfter the addition
  2. filtrationThe mixture was then filtered
  3. customevaporated

Sources & evidence

ORD record
ord-a14f029902a446bc8addbe3fdf4da456
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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