Water → 2-[4-(Chloromethyl)phenyl]-5-methyl-1,3-benzoxazole

HRID 875310Notes

Reaction equation

O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:13][CH2:14][C:15]1[CH:31]=[CH:30][C:18]([C:19]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=2[OH:29])=O)=[CH:17][CH:16]=1.O.CCCCCC>ClC1C=CC=CC=1Cl>[Cl:13][CH2:14][C:15]1[CH:31]=[CH:30][C:18]([C:19]2[O:29][C:23]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=3[N:21]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 175 °C

Procedure

With stirring, 5 g (26.3 mmol) of p-toluenesulphonic acid monohydrate were added to 116 g (about 406 mmol) of 4-(chloromethyl)-N-(2-hydroxy-5-methylphenyl)benzamide in 700 ml of 1,2-dichlor-obenzene. The reaction solution was then heated to 175° C. (oil bath temperature) and stirred at this temperature on a water separator for 3 hours. The reaction solution was then cooled to room temperature, 200 ml of hexane were added and the mixture was stirred for about 1 hour. The precipitated solid was filtered off, washed with hexane and air-dried. This gave 56 g (217.29 mmol, 53% of theory) of the target compound.

Workup

temperatureThe reaction solution was then cooled to room temperature
stirringthe mixture was stirred for about 1 hour
filtrationThe precipitated solid was filtered off
washwashed with hexane
customair-dried

Sources & evidence

ORD record: ord-50ef6970534142bba153e5657b8b8a76
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981104B2

Reaction notes

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