Triethylamine → Phenyl (2-chloropyridin-4-yl)carbamate

HRID 2232174Notes

Reaction equation

HRID 2232174 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 844322-Chloropyridin-4-amine

Product 1

HCID 21247422Phenyl (2-chloropyridin-4-yl)carbamateYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a dry nitrogen atmosphere a solution of 12.0 ml (0.096 mole) of phenyl chloroformate in 300 ml of methylene chloride was added dropwise to a cold (0° C.) stirred solution of 10.2 g (0.079 mole) of 4-amino-2-chloropyridine and 16.5 ml (0.12 mole) of triethylamine in 300 ml of methylene chloride. After complete addition the reaction mixture was allowed to come to room temperature and stirred at room temperature for approximately 18 hours. The mixture was washed with three 100 ml portions of water followed by 100 ml of an aqueous saturated sodium chloride solution. The washed mixture was dried over anhydrous magnesium sulfate and filtered. The filtrate was subjected to column chromatography on silica gel, eluted with acetone:methylene chloride (4:96), to yield 7.4 g of phenyl N-(2-chloro-4-pyridinyl)carbamate as a solid.

Workup

  1. additionAfter complete addition the reaction mixture
  2. customto come to room temperature
  3. washThe mixture was washed with three 100 ml portions of water
  4. dry with materialThe washed mixture was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. washeluted with acetone:methylene chloride (4:96)

Sources & evidence

ORD record
ord-dd8c3fba377e42e9b0879aa7fba34983
Source dataset
uspto-grants-1988_11
Patent number
US04787931

Reaction notes

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