Thionyl Chloride → HCID 20063999, compound

HRID 359807Notes

Reaction equation

HRID 359807 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([NH:15][CH2:16][CH2:17][OH:18])=O)=[CH:11][CH:10]=1.S(Cl)(Cl)=O>CCOCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]2[O:18][CH2:17][CH2:16][N:15]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 200640874-(6-bromohexyloxy)-N-(2-hydroxyethyl)benzamide

Product 1

HCID 20063999HCID 20063999, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 100 g of 4-(6-bromohexyloxy)-N-(2-hydroxyethyl)benzamide was added dropwise 112 g (75 ml) of thionyl chloride over a 20 minute period. The mixture was stirred for 45 minutes and then diluted with several volumes of ether. A solid product separated which was collected and rinsed with ether to give 90 g of 2-[4-(6-bromohexyloxy)phenyl]-4,5-dihydro-oxazole.

Workup

  1. customA solid product separated which
  2. customwas collected
  3. washrinsed with ether

Sources & evidence

ORD record
ord-4e52a1a72c1a4aff8e46ad4c08726396
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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