Dimethyl Sulfate → HCID 137078799, compound

HRID 1482728Notes

Reaction equation

HRID 1482728 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[N:20][C:21]2[CH:22]=[CH:23][C:24]([OH:30])=[C:25]([CH:29]=2)[C:26]([OH:28])=[O:27])=[CH:15][CH:14]=1)=[N+:2]=[N-:3].[C:31](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]=[N:20][C:21]2[CH:22]=[CH:23][C:24]([OH:30])=[C:25]([CH:29]=2)[C:26]([O:28][CH3:31])=[O:27])=[CH:17][CH:18]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 137078798HCID 137078798, compound

Product 1

HCID 137078799HCID 137078799, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 5-((4-(8-azidooctyloxy)phenyl)diazenyl)-2-hydroxybenzoic acid (400 mg, 0.97 mmol) in acetone (20 mL) was added powdered anhydrous potassium carbonate (270 mg, 1.94 mmol). Dimethyl sulfate (92 mg, 0.97 mmol) was then added dropwise at room temperature. The reaction mixture was heated at reflux for 20 min and then allowed to cool to ambient temperature. Volatiles were removed in vacuo, the residue taken up in EtOAc (40 mL), the solution washed with water (2×20 mL), brine, 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 hexanes (95:5) as the elutant to give 210 mg (0.49 mmol, 50%) of the product as a yellow solid, mp 58-60° C. 1H NMR (500 MHz, CDCl3) δ 1.39-1.51 (m, 8H), 1.64 (qt, 2H), 1.83 (qt, 2H), 3.28 (t, J=Hz, 2H), 4.02 (s, 3H), 4.05 (t, J=6.5 Hz, 2H), 7.88 (d, J=Hz, 2H), 8.07 (dd, J=Hz, 2.5 Hz, 1H), 8.42 (d, J=2.5 Hz, 1H), 11.06 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 25.9, 26.7, 28.8, 29.1, 29.2, 51.5, 52.5, 68.2, 112.4, 114.7, 118.3, 124.5, 126.0, 128.7, 145.5, 146.7, 161.5, 163.3, 170.3; HRMS (ESI) calculated for C22H28N5O4 (M+H)+426.2135, observed 426.2141.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 min
  3. customVolatiles were removed in vacuo
  4. washthe solution washed with water (2×20 mL), brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-c84630a5a0ca4a5ba78dbaf946656f63
Source dataset
uspto-grants-2016_08
Patent number
US09415110B1

Reaction notes

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