HCID 67387541, compound → HCID 25104749, compound

HRID 238556Notes

Reaction equation

HRID 238556 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([N:8]([CH3:20])[C:9]([C:11]2[CH:19]=[CH:18][C:14]3=[N:15][O:16][N:17]=[C:13]3[CH:12]=2)=[O:10])[CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH3:20][N:8]([CH:4]1[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH2:3]1)[C:9]([C:11]1[CH:19]=[CH:18][C:14]2=[N:15][O:16][N:17]=[C:13]2[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 67387541HCID 67387541, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 25104749HCID 25104749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

N-(3-Hydroxycyclohexyl)-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide (0.38 g, 1.38 mmol) was dissolved in dichloromethane (10 ml) and PCC (3 g) was added and the mixture stirred for 3 h at 20° C. The solvent was evaporated onto silica gel and the product chromatographed on silica gel eluting with ethyl acetate/chloroform (3:1) to give the title product as a white solid after trituration with diethyl ether (0.19 g). Mp=164-165° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.93 (d, J=9.3 Hz, 1H); 7.84 (s, 1H); 7.40 (d, J=9.3 Hz, 1H); 4.90-4.67 and 4.00-3.75 (m, 1H); 3.00 (sb, 3H); 2.71-1.30 ppm (s, 8H).

Workup

  1. customThe solvent was evaporated onto silica gel
  2. customthe product chromatographed on silica gel eluting with ethyl acetate/chloroform (3:1)

Sources & evidence

ORD record
ord-83075f2ac014413ca445b61ab636b744
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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