tert-Butyl methyl ether → Phenyl isocyanate

HRID 7226Notes

Reaction equation

HRID 7226 reaction equation
ClC1N=C(Cl)C([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][CH:12]=2)=CN=1.C[O:20]C(C)(C)C>>[C:11]1([N:10]=[C:9]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 21939303[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine

Product 1

HCID 7672Phenyl isocyanate

Conditions

Temperature
55 °C

Procedure

A 500-mL, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with [(2,4-dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine (59.6 g, 209.7 mmol) (from Example 1d supra) and tert-butyl methyl ether (300 mL) (Aldrich). After heating to 55° C. to give a clear solution, phenyl isocyanate (27.48 g, 230.7 mmol) (Aldrich) was added and the mixture was heated to reflux for 10 hours. TLC analysis indicated essentially complete reaction. After cooling to room temperature, the resulting solid was collected by filtration, washed with tert-butyl methyl ether (100 mL), and dried by suction to give N-[(2,4-dichloropyrimidin-5-yl)methyl]-N-(4-methoxyphenyl)(phenylamino) carboxamide as white crystals; 98.46% pure by HPLC analysis. (Yield 78.8 g, 91.3%).

Workup

  1. customA 500-mL, three-necked flask equipped with a mechanical stirrer

Sources & evidence

ORD record
ord-92a54a1510ba4d6ba7f20261138b43f7
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Reaction notes

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