2,5-Dichlorophenol → HCID 86587539, compound

HRID 2183833Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].O[CH:11]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:11]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

2,5-Dichlorophenol (163 mg, 1.00 mmol) and (3-hydroxyheptyl)methylcarbamic acid, 1,1-dimethylethyl ester (360 mg, 1.47 mmol) were dissolved in tetrahydrofuran (10 ml). To the resulting solution was added tributylphosphine (0.380 ml, 1.50 mmol) and then 1,1′-(azodicarbonyl)dipiperidine (380 mg, 1.50 mmol). The solution was then heated to 50° C. under nitrogen for 3 h, and then allowed to stir at room temperature for a further 20 h. The mixture was then filtered and poured into sodium hydrogen carbonate solution. The mixture was extracted with diethyl ether three times and the combined organic fractions were washed with brine, then dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 10% ethyl acetate/isohexane as eluent to give 200 mg (51%) of the title compound as an oil.

Workup

filtrationThe mixture was then filtered
additionpoured into sodium hydrogen carbonate solution
extractionThe mixture was extracted with diethyl ether three times
washthe combined organic fractions were washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
washthe residue eluted down a flash chromatography column

Sources & evidence

ORD record: ord-69ffd8e48044483fa06f0e364aeaf9d2
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900243B2

Reaction notes

Loading…