Toluene → tert-Butyl (6-(chloromethyl)pyridin-2-yl)carbamate

HRID 243553Notes

Reaction equation

HRID 243553 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:9])[N:3]=1.[C:10]1([CH3:16])[CH:15]=CC=C[CH:11]=1.ClC(Cl)([O:20][C:21](=O)[O:22]C(Cl)(Cl)Cl)Cl.[OH-].[Na+]>O.C(O)(C)(C)C>[C:10]([O:22][C:21](=[O:20])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:9])[N:3]=1)([CH3:16])([CH3:15])[CH3:11]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 75539601HCID 75539601, compound

Product 1

HCID 21851761tert-Butyl (6-(chloromethyl)pyridin-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2.43 g (10 millimoles) of 2-amino-6-chloromethylpyridine, toluene (30 mL), 10 mL of t-butyl alcohol and 1.48 g (5 millimoles) of triphosgene were added to a reaction system followed by refluxing for 1 hour. Water and 28% sodium hydroxide were sequentially added while holding the internal temperature at 0° C. or lower. After separating the liquid, the aqueous phase was extracted with ethyl acetate. The organic phases were combined and mixed. A portion of the organic phase was sampled and subjected to quantitative analysis by HPLC. The target (6-chloromethyl-pyridin-2-yl)-carbamic acid tert-butyl ester was not formed at all. 1,3-bis-(6-chloromethyl-pyridin-2-yl)-urea (urea compound) constituted the main product.

Workup

  1. temperatureby refluxing for 1 hour
  2. customat 0° C.
  3. customAfter separating the liquid
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. additionmixed
  6. aliquotA portion of the organic phase was sampled

Sources & evidence

ORD record
ord-b2cc25023c02427baf33cdab7dc245db
Source dataset
uspto-grants-2014_02
Patent number
US08653269B2

Reaction notes

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