Aluminium lithium hydride → HCID 58265121, compound

HRID 1818940Notes

Reaction equation

HRID 1818940 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])=[N:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=2)=[O:12])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86603173HCID 86603173, compound

Product 1

HCID 58265121HCID 58265121, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 44.2 (10 mmol) in dry THF (50 mL) was added lithium aluminum hydride (“LAH”; 30 mmol; 1.0 M in THF) at room temperature. After stirring for 30 minutes, the reaction mixture was cooled and treated with the cautious addition of ice water. The solvent was removed, diluted with saturated sodium bicarbonate and extracted with EtOAc. The organic layers were combined, dried, concentrated and purified by flash column chromatography on silica gel to provide 1-[5-(2-hydroxy-ethyl)-thiazol-2-yl]-3-(3-trifluoromethyl-phenyl)-urea (compound 44.3) in 95% yield. EIMS (m/z): calcd. for C13H12F3N3O2S (M+)+H 332.06. found 332.10.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe solvent was removed
  3. additiondiluted with saturated sodium bicarbonate
  4. extractionextracted with EtOAc
  5. customdried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-367a0f8c8b6d44e2bb279c484341bc2c
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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