2-Chloroaniline → HCID 58970390, compound

HRID 1678044Notes

Reaction equation

HRID 1678044 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].ClOC(C)(C)C.[CH3:15][S:16][CH:17]([C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=1)[CH3:18].C[O-].[Na+]>ClCCl.O.CO>[CH3:15][S:16][C:17]([C:19]1[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[N:24]=1)([C:5]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[C:3]=1[NH2:4])[CH3:18]

Participants

8

Reactant 4

HCID 72402-ChloroanilineHCID 521297Tert-Butyl hypochloriteHCID 10942334Sodium MethoxideHCID 58970391HCID 58970391, compound

Product 1

HCID 58970390HCID 58970390, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-65 °C

Procedure

2-Chloroaniline 7 g (32.7 mmol) was dissolved in dichloromethane 100 ml and the solution was cooled to −65° C. To the solution a solution of t-butyl hypochlorite 3.55 g (32.7 mmol) in dichloromethane 10 ml was added dropwise and the solution was stirred at the same temperature for 10 minutes. Then a solution of 2-(1-methylthioethyl)-4,6-dimethoxypyrimidine in dichloromethane was added thereto dropwise and the solution was stirred at the same temperature for 1 hour. After a methanol solution of sodium methoxide 12.6 g (65.3 mmol) had been added dropwise and the mixed solution had been stirred at the same temperature for 10 minutes, the reaction solution was stirred until it came to room temperature. The reaction solution was poured into water and extracted with dichloromethane. The solvent was distilled off and the residue was purified with column chromatography (hexane/ethyl acetate=5/1) to obtain 2-{1-methylthio-1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 10.0 g (90%).

Workup

  1. stirringdropwise and the solution was stirred at the same temperature for 1 hour
  2. stirringthe mixed solution had been stirred at the same temperature for 10 minutes
  3. stirringthe reaction solution was stirred until it
  4. customcame to room temperature
  5. extractionextracted with dichloromethane
  6. distillationThe solvent was distilled off
  7. customthe residue was purified with column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ab3365f631b4493c95169466faad38ad
Source dataset
uspto-grants-2011_08
Patent number
US08008484B2

Reaction notes

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