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

HRID 332153

Reaction equation

HRID 332153 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1.O=S(Cl)[Cl:19]>C(Cl)Cl>[Cl:19][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:4]=1

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-dcd17301f80c4a4196d672f9fbb71d79
Source dataset
uspto-grants-2014_11
Patent number
US08877804B2

Linked notes

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