Sodium Azide → HCID 86608648, compound

HRID 1455061Notes

Reaction equation

HRID 1455061 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]3)=[CH:10][CH:11]=1)=[O:4].[N-:29]=[N+:30]=[N-:31].[Na+]>C(#N)C>[N:29]([CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[O:19][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]3)=[CH:10][CH:11]=1)=[O:4])=[N+:30]=[N-:31]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10046189HCID 10046189, compound

Product 1

HCID 86608648HCID 86608648, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]acetamide (500 mg), sodium azide (445 mg) and acetonitrile were mixed. Reaction mixture was refluxed for 3 hours. After cooling into room temperature, the reaction mixture was filtered and the filtrate was evaporated to the dryness. 1H-NMR (400 MHz; d6-DMSO) δ: 10.3 (s, 1H), 8.29 (d, 1H, J 2.7 Hz), 8.03 (dd, 1H, J 2.7, 8.8 Hz), 7.47-7.33 (m, 5H), 6.96 (d, 1H, J 8.8 Hz), 6.88-6.85 (m, 3H), 5.12 (dd, 1H, J 2.20, 10.1 Hz), 4.07 (s, 2H), 3.00-2.92 (m, 1H), 2.76-2.70 (m, 1H), 2.19-2.14 (m, 1H), 2.02-1.97 (m, 1H).

Workup

  1. customReaction mixture
  2. temperaturewas refluxed for 3 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated to the dryness

Sources & evidence

ORD record
ord-a7afdff5d61b44e0997730e973624cf1
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

Loading…