Dichloromethane → HCID 21071328, compound

HRID 1371828Notes

Reaction equation

HRID 1371828 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)=[N:2]1.ClCCl.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>N1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:17](=[O:18])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8][CH:7]=2)=[N:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 231185764-(1,2-Oxazol-3-yl)aniline2×

Product 1

HCID 21071328HCID 21071328, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Isoxazol-3-ylphenylamine (Intermediate 5, 4 g, 24.69 mmol) was added to dichloromethane (20 ml) followed by pyridine (4.6 ml). The solution was cooled to 0° C. and benzyl chloroformate (5.27 ml, 37.02 mmol) was added drop wise. The solution was allowed to stir for 2 hours at room temperature and then concentrated under vacuum. The residue was added to 30 ml of 1:1 hexane:EtOAc mixture. The crystals were collected by filtration to yield the product (2.26 g).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was added to 30 ml of 1:1 hexane
  3. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-ad7a3b79debc45c28bbc9e54e710f215
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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