Triethylamine → Phenyl N-(4-Chloro-3-(pyrid-3-yl)phenyl)carbamate

HRID 1603785Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.C(N(CC)CC)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C(O)(C)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:23](=[O:24])[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -40 °C

Procedure

4-Chloro-3-(pyrid-3-yl)aniline (0.08 g, 0.00039 mole) in isopropyl alcohol (8 ml) was cooled to -40° C. and treated under argon with triethylamine (0.06 ml, 0.00043 mole) followed dropwise by phenyl chloroformate (0.051 ml, 0.00041 mole). The reaction mixture was stirred at -40° C. for half an hour and allowed to warm to ambient temperature. The solvent was removed in vacuo and the residue dissolved in dichloromethane, washed with HO, dried (Na2SO4) and evaporated in vacuo to afford the title compound (0.12 g, 95%) as an orange solid.

Workup

temperatureto warm to ambient temperature
customThe solvent was removed in vacuo
dissolutionthe residue dissolved in dichloromethane
washwashed with HO
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-45b61a2e5dc2487a8a30cf7224996c5e
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990133

Reaction notes

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