Diisopropyl Ether → HCID 86649592, compound

HRID 1530041Notes

Reaction equation

HRID 1530041 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH2:7][O:8][S:9]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])(=[O:11])=[O:10].C(OC(C)C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:18][C:17]1[CH:16]=[C:15]([CH3:19])[CH:14]=[C:13]([CH3:20])[C:12]=1[S:9]([O-:11])(=[O:10])=[O:8].[NH2:7][N+:6]1[CH:5]=[CH:4][S:3][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 771292-MethylthiazoleHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 86649592HCID 86649592, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

To a solution of 2-methyl-1,3-thiazole (6.6 g, 67 mmol) in toluene (60 mL) was added a solution of 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene obtained in the above in ethyl acetate-toluene under ice-cooling, and the mixture was stirred for 2 hr. Diisopropyl ether (200 mL) was added to the reaction system, and the resulting solid was collected by filtration to give the title compound (13 g, 63%) as a white solid. The filtrate was concentrated under reduced pressure to about 100 mL, diisopropyl ether (100 mL) was added, and the resulting solid was collected by filtration to give the title compound (3.8 g, 18%) as a white solid (total yield 81%).

Workup

  1. temperaturecooling
  2. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-e0da8cd9884a4dce8ebde691fb2c7c78
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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