Triphenylphosphine → HCID 86687932, compound

HRID 2401477Notes

Reaction equation

HRID 2401477 reaction equation
[NH2:1][C:2]1[C:14]([Cl:15])=[CH:13][C:5]([C:6]([N:8]([CH2:10][CH2:11]O)[CH3:9])=[O:7])=[C:4]([OH:16])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[NH2:1][C:2]1[C:14]([Cl:15])=[CH:13][C:5]2[C:6](=[O:7])[N:8]([CH3:9])[CH2:10][CH2:11][O:16][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86687930HCID 86687930, compound

Product 1

HCID 86687932HCID 86687932, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-5-chloro-2-hydroxy-N-(2-hydroxyethyl)-N-methylbenzamide (300 mg, 1.22 mmol) was stirred in dichloromethane at 0° C. under an atmosphere of nitrogen then TEA (247 mg, 2.4 mmol), triphenylphosphine (320 mg, 1.2 mmol) and DEAD (212 mg, 1.2 mmol) were added. The reaction was allowed to stir for 1 h at 0° C., after which time LCMS indicated the formation of a peak consistent with the target material. The volatiles were removed under reduced pressure and the resulting gum was dissolved in dichloromethane then passed through a SCX-2 20 g cartridge. The cartridge was washed with dichloromethane-methanol 10% and the fractions were collected in 100 mL flasks. TLC indicated that the fractions were not identical in composition which was verified by LCMS. The purest fraction was concentrated to afford the target material (18 mg, 5%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe resulting gum was dissolved in dichloromethane
  3. washThe cartridge was washed with dichloromethane-methanol 10%
  4. customthe fractions were collected in 100 mL flasks
  5. concentrationThe purest fraction was concentrated

Sources & evidence

ORD record
ord-c20216cdb86d4f90b5262e4109947c03
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

Loading…