Phenyl chloroformate → phenyl 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate

Reaction equation

[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([C:8]([F:11])([F:10])[F:9])=[N:3]1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>>[CH3:1][N:2]1[C:6]([NH:7][C:13](=[O:14])[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:5][C:4]([C:8]([F:9])([F:10])[F:11])=[N:3]1

Participants

Reactant 2

HCID 15891Phenyl chloroformate

HCID 196233031-methyl-3-(trifluoromethyl)-1H-pyrazol-5-amine

Product 1

HCID 66876388phenyl 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamateYield 26%

Procedure

Using the procedure described in Example 161C, 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (1.70 g, 10.3 mmol) and phenyl chloroformate (1.88 g, 12 mmol) were reacted to afford phenyl 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate as solid (0.760 g, 26%). LC-MS (ESI) m/z 286 (M+H)+.

Workup

customwere reacted

Sources & evidence

ORD record: ord-81d0ebbc98814d9aab89301eb8080ba9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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