Dimethylamine → 2-Tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide

HRID 1050980Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][NH:9][CH3:10].[C:11]([C:15]1[O:16][C:17]2[C:23]([S:24](Cl)(=[O:26])=[O:25])=[C:22]([Cl:28])[CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:14])([CH3:13])[CH3:12].O>O1CCCC1>[CH3:8][N:9]([CH3:10])[S:24]([C:23]1[C:17]2[O:16][C:15]([C:11]([CH3:13])([CH3:12])[CH3:14])=[N:19][C:18]=2[CH:20]=[CH:21][C:22]=1[Cl:28])(=[O:25])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

12.9 ml (93 mmol; 3.0 eq) of triethylamine and 93 ml of 2 M dimethylamine in tetrahydrofuran were added dropwise to a solution of 9.55 g (31 mmol; 1.0 eq) of 2-tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride in 200 ml of tetrahydrofuran cooled to 0° C. The reaction medium was stirred at 0° C. for 3 hours and was then treated with water. The reaction medium was extracted with ethyl acetate. The organic phases were combined, washed with water, dried over magnesium sulfate, filtered and evaporated. 9.12 g of 2-tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide were obtained in the form of a beige solid. Yield=93%.

Workup

extractionThe reaction medium was extracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-34117f0ee92d4c009f760ed6ee7a9f08
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

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