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

HRID 989196
Notes
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Reaction equation

HRID 989196 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 (0.051 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-27cac9000ff6488c90442d329a4f7fb7
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06638953B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes