Isopropenyl chloroformate → Prop-1-en-2-yl 3-(trifluoromethyl)isoxazol-5-ylcarbamate

HRID 1930341Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[C:3]1[CH:7]=[C:6]([NH2:8])[O:5][N:4]=1.Cl[C:12]([O:14][C:15]([CH3:17])=[CH2:16])=[O:13].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>>[F:1][C:2]([F:10])([F:9])[C:3]1[CH:7]=[C:6]([NH:8][C:12](=[O:13])[O:14][C:15]([CH3:17])=[CH2:16])[O:5][N:4]=1

Participants

Reactant 3

HCID 93846Isopropenyl chloroformate

HCID 2733832Lithium Hexamethyldisilazide

HCID 139139963-(Trifluoromethyl)-1,2-oxazol-5-amine

Product 1

HCID 69299521Prop-1-en-2-yl 3-(trifluoromethyl)isoxazol-5-ylcarbamateYield 38.2%

Procedure

Using general method G, 3-(trifluoromethyl)isoxazol-5-amine (1.38 g, 9.1 mmol) and isopropenyl chloroformate (1.1 g, 9.1 mmol) in presence of LiHMDS (1.0M, 18 mL, 18.2 mmol) were combined to afford prop-1-en-2-yl 3-(trifluoromethyl)isoxazol-5-ylcarbamate (0.82 g, 38% yield).). 1H NMR (400 MHz, DMSO-d6): δ 12.3 (s, 1H), 6.48 (s, 1H), 4.83 (m, 1H), 4.80 (m, 1H), 1.93 (s, 3H); MS (ESI) m/z: 237.0 (M+H+).

Sources & evidence

ORD record: ord-6e1fece7dd114a8c8d56403bcd7b0ee2
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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