Water → Phenyl 6-methoxypyridin-3-ylcarbamate

HRID 496284

Reaction equation

HRID 496284 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:16]1([O:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl>[C:16]1([O:22][C:23](=[O:24])[NH:9][C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 20185962Phenyl 6-methoxypyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Methoxy-pyridin-3-ylamine (1.0 g, 8.06 mmol) and pyridine (18 ml) are stirred in dry CH2Cl2. To this mixture phenylchloroformate (1.9 g, 12.0 mmol) is added and stirred for 24 hours at room temperature. Water and a solution of 1:1 EtOAc/hexanes is added to the mixture and the organic layer is separated. The organic layer is washed with 1N HCl three times and with brine once. The organic layer is dried over Na2SO4, filtered, and evaporated in vacuo. Purify by flash column chromatography (0-10% EtOAc/CH2Cl2) to obtain (6-methoxy-pyridin-3-yl)-carbamic acid phenyl ester. Mass spec.: m+1=245 (AP+). B. 1′-(6-methoxy-pyridin-3-yl-carbamoyl)-spiroisobenzofuran-1,4′-piperidine

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with 1N HCl three times and with brine once
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurify by flash column chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-f8acd6879bec43138282c3654376f1d2
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Linked notes

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