Pyridine → HCID 86691781, compound

HRID 1750312Notes

Reaction equation

HRID 1750312 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[C:12](Cl)(=[O:19])[O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16].N1C=CC=CC=1>ClCCl>[Cl:16][C:15]([Cl:18])([Cl:17])[CH2:14][O:13][C:12](=[O:19])[NH:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][O:7][C:8]2=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 936316-Aminophthalide

Product 1

HCID 86691781HCID 86691781, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 6-aminoisobenzofuran-1(3H)-one 1 (Maybridge, 13.43 g, 90 mmol) in dichloromethane (DCM, 200 mL) at 0° C. was added 2,2,2-trichloroethyl carbonochloridate 1a (18.23 mL, 135 mmol) and pyridine (17.79 mL, 180 mmol). The reaction mixture was stirred at room temperature (RT, ca. 25° C.) for 1 h. Thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) showed the reaction was complete. The reaction mixture was filtered and washed with DCM (2×30 mL) to afford carbamate 2 as a white solid (17.03 g, 58%). LCMS: [M+1]=324.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM (2×30 mL)

Sources & evidence

ORD record
ord-47e5abf5c4884e6f8ef2ee9bc0dd5a26
Source dataset
uspto-grants-2015_10
Patent number
US09156850B2

Reaction notes

Loading…