Ethyl Acetate → (3-Fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea

HRID 1685016Notes

Reaction equation

HRID 1685016 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7](=[O:17])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([O-])=[O:15])[N:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[Na+].CCOC(C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)=[O:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 866612832-(3-(3-Fluorobenzyl)ureido)thiazole-4-carboxylate

Product 1

HCID 86661282(3-Fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-ureaYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-(3-(3-fluorobenzyl)ureido)thiazole-4-carboxylate (4.08 mmol) is taken up in THF and solution is cooled to −78° C. Added LiAlH4 (2.6 equivalents, 1M solution in THF). Stir at ambient temperature for 3 hours. Add slowly Na2SO4.10H2O (6.4 g), then NaHSO4 (1.8 g). Stir for 30 hours. Aqueous workup with EtOAc. Crystallized from DCM/hexanes to give 1-(3-fluorobenzyl)-3-(4-(hydroxymethyl)thiazol-2-yl)urea in 79% yield.

Workup

  1. stirringStir for 30 hours
  2. customCrystallized from DCM/hexanes

Sources & evidence

ORD record
ord-79e865f2db5a41158e70bd9df6b4d227
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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