Ethyl chloroformate → HCID 67634056, compound

HRID 1456361Notes

Reaction equation

C(=O)([O-])O.[Na+].[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[C:9]([NH2:24])=[N:8]1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O1CCCC1.O>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:14]=2)[C:9]([NH:24][C:26](=[O:27])[O:28][CH2:29][CH3:30])=[N:8]1

Participants

Conditions

Temperature: 25 °C

Procedure

9.8 g of sodium hydrogen carbonate (0.117 mol) are added to a solution of 19.7 g (0.078 mol) of 1-methyl-6-(phenylmethoxy)-1H-indazol-3-amine in 200 ml of a 9:1 mixture of tetrahydrofuran/water, and then 8.9 ml (0.093 mol) of ethyl chloroformate are added dropwise while maintaining the temperature at 25° C. A milky suspension is obtained which is left with stirring for 30 minutes, and then the solvent is evaporated off under reduced pressure. The residue is treated with dichloromethane and water. The organic phase is decanted off, dried over sodium sulphate and concentrated under reduced pressure. The product is crystallized from diisopropyl ether. 20.1 g of product are obtained.

Workup

customA milky suspension is obtained which
waitis left
customthe solvent is evaporated off under reduced pressure
additionThe residue is treated with dichloromethane and water
customThe organic phase is decanted off
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe product is crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-71dd4c8d14384dc0b1bf089fc774e43e
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843975

Reaction notes

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