Potassium Iodide → HCID 90142392, compound

HRID 1483039Notes

Reaction equation

HRID 1483039 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].Br[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].CC(C)([O-])C.[K+].[I-].[K+]>CN(C=O)C>[O:10]=[C:2]1[N:3]([CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 60432(3H)-BenzoxazoloneHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 90142392HCID 90142392, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Combine 2-(3H)-benzoxazolone (0.4 g, 2.9 mmol), tert-butyl 2-bromoethylcarbamate (715.14 mg, 3.19 mmol), potassium tert-butoxide (508.7 mg, 4.35 mmol), potassium iodide (0.1 g, 0.6 mmol) in DMF (6 mL). Heat to 80° C. and stir the mixture overnight. Filter; collect the filtrate; and purify via HPLC conditions M (See below) to provide the title compound (0.53 g, 65.6%) as an oily solid. MS (m/z): 223 (M-tBu+1).

Workup

  1. filtrationFilter
  2. customcollect the filtrate
  3. customand purify via HPLC conditions M (See below)

Sources & evidence

ORD record
ord-c68224ae532643459fb3c308ed672a5c
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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