4-Chlorophenyl chloroformate → 4-Chlorophenyl 5-(2-fluoropropan-2-yl)isoxazol-3-ylcarbamate

HRID 871484Notes

Reaction equation

HRID 871484 reaction equation
[F:1][C:2]([C:5]1[O:9][N:8]=[C:7]([NH2:10])[CH:6]=1)([CH3:4])[CH3:3].Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:13]>>[F:1][C:2]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:12](=[O:13])[O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:6]=1)([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 1390594-Chlorophenyl chloroformateHCID 668765605-(2-Fluoropropan-2-yl)isoxazol-3-amine

Product 1

HCID 569543154-Chlorophenyl 5-(2-fluoropropan-2-yl)isoxazol-3-ylcarbamateYield 100%

Procedure

Prepared from 5-(2-fluoropropan-2-yl)isoxazol-3-amine (40 mg, 0.278 mmol) and 4-chlorophenyl chloroformate (54 mg, 0.28 mmol) according to the procedure described in Example 122A Step 3, to afford 4-chlorophenyl 5-(2-fluoropropan-2-yl)isoxazol-3-ylcarbamate as a colorless solid (83 mg, 100%). 1H NMR (300 MHz, CDCl3) δ 8.11 (brs, 1H), 7.36-7.40 (m, 2H), 7.12-7.17 (m, 2H), 6.83 (s, 1H), 1.76 (d, J=21 Hz, 6H); LC-MS (ESI) m/z 299 (M+H)+.

Sources & evidence

ORD record
ord-fa576a0678f44fb98ce24024aa1b5a76
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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