Pyridine → (4-Methoxy-benzooxazol-2-yl)-carbamic acid methyl ester

HRID 1611932Notes

Reaction equation

HRID 1611932 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:20]([O:22][CH3:23])=[O:21]>ClCCl>[CH3:23][O:22][C:20](=[O:21])[NH:12][C:10]1[O:11][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 222522444-Methoxybenzo[d]oxazol-2-amine

Product 1

HCID 23593639(4-Methoxy-benzooxazol-2-yl)-carbamic acid methyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 65 g (40 mmol) 4-methoxy-benzooxazol-2-yl-amine and 4.5 ml (56 mmol) pyridine in 250 ml dichoromethane at 0° C. was added dropwise a solution of 4.1 ml (49 mmol) methyl chloroformate in 50 ml dichoromethane and stirring continued for 3.5 hours. The mixture was then poured onto water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (dichloromethane) afforded 4.7 g (54%) (4-methoxy-benzooxazol-2-yl)-carbamic acid methyl ester as an off-white crystalline solid. EI-MS m/e (%): 222 (M+, 100), 190 (27), 163 (23).

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48e760b7a21247c09e633ead2d9a5840
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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