Sodium Azide → HCID 137078798, compound

HRID 1482727Notes

Reaction equation

HRID 1482727 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[N:18][C:19]2[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([CH:27]=2)[C:24]([OH:26])=[O:25])=[CH:13][CH:12]=1.[N-:29]=[N+:30]=[N-:31].[Na+]>CS(C)=O.CCOC(C)=O>[N:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[N:18][C:19]2[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([CH:27]=2)[C:24]([OH:26])=[O:25])=[CH:13][CH:12]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 137078800HCID 137078800, compound

Product 1

HCID 137078798HCID 137078798, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-((4-(8-Bromooctyloxy)phenyl)diazenyl)-2-hydroxybenzoic acid (2.50 g, 5.6 mmol) was dissolved in DMSO (40 mL) and NaN3 (1.10 g, 16.9 mmol) was added slowly to the reaction mixture with stirring at room temperature. After 48 h, the mixture was diluted with EtOAc (100 mL), washed with water (4×20 mL), brine (20 mL), dried over Na2SO4, and filtered. Volatiles were removed in vacuo and the residue subjected to column chromatography on silica gel 60 (230-400 mesh) using EtOAc and methanol (98:2) as the elutant to give 2.10 g (5.1 mmol, 91%) of the product as a red-brown solid, mp 54-56° C. 1H NMR (500 MHz, CDCl3) δ 1.27-1.58 (m, 8H), 1.62-1.64 (m, 2H), 1.81-1.86 (m, 2H), 3.31 (t, J=5 Hz, 2H), 4.06 (t, J=6.5 Hz, 2H), 6.88-7.01 (m, 3H), 7.84 (d, J=10 Hz, 2H), 7.91 (dd, J=15 Hz, 2.5 Hz, 1H), 8.47 (d, J=2.5 Hz, 1H); 13C NMR (125 MHz, CDCl3+CD3OD) δ 22.0, 25.3, 25.4, 28.5, 28.6, 28.8, 31.2, 50.8, 67.7, 114.1, 116.5, 117.5, 123.6, 126.2, 144.6, 146.2, 160.7, 175.0; HRMS (ESI) calculated for C21H26N5O4 (M+H)+412.1979, observed 412.1971.

Workup

  1. washwashed with water (4×20 mL), brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-32d3265547f4410489e589382cdf38e2
Source dataset
uspto-grants-2016_08
Patent number
US09415110B1

Reaction notes

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