Thionyl Chloride → HCID 86701816, compound

HRID 338659Notes

Reaction equation

HRID 338659 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][S:7]2(=[O:12])=[O:11].S(Cl)([Cl:15])=O>ClCCl>[ClH:15].[Cl:15][CH2:2][CH2:3][N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][S:7]2(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86701815HCID 86701815, compound

Product 1

HCID 86701816HCID 86701816, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of (1S,4S)-5-(2-hydroxyethyl)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide (80 mg, 0.418 mmol) and thionyl chloride (0.153 mL, 2.092 mmol) in dichloromethane (2 mL) was stirred at 20° C. for 16 hours. The reaction mixture was concentrated under reduced pressure to provide the title compound (90 mg, 87% yield) as a yellow solid. LCMS: m/e 210.02 (M+H)+, 1.76 min (method 2).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f0389c09d1d46aca82cbbb738d38e6a
Source dataset
uspto-grants-2014_11
Patent number
US08889854B2

Reaction notes

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