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Water → Methyl-phenyl-carbamic Acid 5-(3,4-dichloro-phenoxy)-pyrimidin-2-yl Ester

HRID 1179877
Notes
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Reaction equation

HRID 1179877 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][C:6]1[CH:7]=[N:8][C:9]([OH:12])=[N:10][CH:11]=1.[CH3:17][N:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20].N12CCN(CC1)CC2.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[O:5][C:6]1[CH:11]=[N:10][C:9]([O:12][C:19](=[O:20])[N:18]([CH3:17])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178517841HCID 178517841, compound

Product 1

HCID 69518926Methyl-phenyl-carbamic Acid 5-(3,4-dichloro-phenoxy)-pyrimidin-2-yl EsterYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of 5-(3,4-dichloro-phenoxy)-pyrimidin-2-ol (0.51 g, 2.00 mmol), N-methyl-N-phenylcarbamoyl chloride (0.34 g, 2.00 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.22 g, 2.00 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 1 hour. Water was added and the precipitates were collected by suction. The solids were dissolved in dichloromethane and the solution was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was crystallised from ethyl acetate:heptane yielding the title compound (0.51 g, 65% yield) as an off-white solid.

Workup

  1. customthe precipitates were collected by suction
  2. dissolutionThe solids were dissolved in dichloromethane
  3. dry with materialthe solution was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-d42fde9100064f73b3a6c0b00d59fff9
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07279470B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes