Thionyl Chloride → tert-butyl N-(4-(chloromethyl)pyridin-2-yl)carbamate

HRID 1631223

Reaction equation

HRID 1631223 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].O=S(Cl)[Cl:19]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][Cl:19])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridine

Product 1

HCID 21068467tert-butyl N-(4-(chloromethyl)pyridin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl(4-(hydroxymethyl)pyridin-2-yl)carbamate (600 mg, 2.679 mmol) was first treated with SOCl2 (3 ml) in CH2Cl2 (5 ml) at rt for 2 hrs. The solvent was removed to get a crude tert-butyl(4-(chloromethyl)pyridin-2-yl)carbamate. Then following General Procedure A, the title compound (667 mg, 68%) was prepared from 2-amino-4-chlorobenzenethiol (641 mg, 4.019 mmol), K2CO3 (1.8 g, 13.39 mmol) in DMF (20 ml).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-1c19d27a4f7e40329187a3d81e899c27
Source dataset
uspto-grants-2014_07
Patent number
US08791161B2

Linked notes

Loading…