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Triethylamine → Phenyl N-(4-Chloro-3-(pyrid-3-yl)phenyl)carbamate

HRID 1977758
Notes
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Reaction equation

HRID 1977758 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.C(N(CC)CC)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C(O)(C)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:23](=[O:24])[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 121019664-Chloro-3-(pyrid-3-yl)aniline

Product 1

HCID 18005115Phenyl N-(4-Chloro-3-(pyrid-3-yl)phenyl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-40 °C

Procedure

4-Chloro-3-(pyrid-3-yl)aniline (0.08 g, 0.00039 mole) in isopropyl alcohol (8 ml) was cooled to −40° C. and treated under argon with triethylamine (0.06 ml, 0.00043 mole) followed dropwise by phenyl chloroformate (0051 ml, 0.00041 mole). The reaction mixture was stirred at −40° C. for half an hour and allowed to warm to ambient temperature. The solvent was removed in vacuo and the residue dissolved in dichloromethane, washed with H2O, dried (Na2SO4) and evaporated in vacuo to afford the title compound (0.12 g, 95%) as an orange solid.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with H2O
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-93659ba6fa4b4faaba4c69ea68da6b60
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06235758B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes