Thionyl Chloride → HCID 19809486, compound

HRID 374257Notes

Reaction equation

HRID 374257 reaction equation
O[CH2:2][C:3]1[O:4][C:5]([C:8]23[CH2:15][N:12]([CH2:13][CH2:14]2)[CH2:11][CH2:10][CH2:9]3)=[CH:6][N:7]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[ClH:18].[Cl:18][CH2:2][C:3]1[O:4][C:5]([C:8]23[CH2:15][N:12]([CH2:13][CH2:14]2)[CH2:11][CH2:10][CH2:9]3)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19809494HCID 19809494, compound

Product 1

HCID 19809486HCID 19809486, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (±)5-(2-hydroxymethyl-1,3-oxazol-5-yl)-1-azabicyclo[3.2.1]octane (E10) (0.3g, 1.4 mmol) in absolute chloroform (10 ml) under nitrogen, cooled in ice was treated with thionyl chloride (0.31 ml, 4.3 mmole) over 5 minutes. The reaction was allowed to warm up to room temperature over 45 minutes. Evaporation of solvent in vacuo afforded the title compound (D25) as a brown solid (380 mg, 100%) which was used without purification.

Workup

  1. customEvaporation of solvent in vacuo

Sources & evidence

ORD record
ord-1f28903f96064506b6ef661aca649bc4
Source dataset
uspto-grants-1992_11
Patent number
US05166357

Reaction notes

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