Chloromethyl Methyl Ether → HCID 25228375, compound

HRID 1920676Notes

Reaction equation

HRID 1920676 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10]Cl.[OH:12][C:13]1[C:22]([C:23]#[N:24])=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([CH3:25])=[N:20]2)=[CH:15][CH:14]=1>CC(C)=O>[CH3:8][O:9][CH2:10][O:12][C:13]1[C:22]([C:23]#[N:24])=[C:21]2[C:16]([CH:17]=[CH:18][C:19]([CH3:25])=[N:20]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 135858969HCID 135858969, compound

Product 1

HCID 25228375HCID 25228375, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Referring to FIG. 20, under a nitrogen atmosphere, triethylamine (0.034 mL, 0.235 mmol) and chloromethyl methyl ether (0.018 mL, 0.235 mmol) were added to a solution of 5b (0.0200 g, 0.109 mmol) in acetone (8 mL). The reaction was stirred for 1 h. The solvent was evaporated and the remaining residue was dissolved in chloroform, which was washed with brine, dried over Na2SO4, and evaporated to afford 8b (0.0236 g, 0.106 mmol, 97%) as a white solid: 1H NMR (CDCl3) δ 8.02 (1H, d, J=8.0 Hz), 7.93 (1H, d, J=9.2 Hz), 7.48 (1H, d, J=9.2 Hz), 7.29 (1H, d, J=8.4 Hz), 5.43 (2H, s), 3.58 (3H, s), 2.79 (3H, s); 13C NMR (CDCl3) δ 162.4, 161.8, 148.7, 135.9, 133.4, 121.8, 121.7, 114.6, 114.9, 95.1, 56.9, 25.7; FTIR (neat) 2924, 2216, 1612, 1504, 1248, 1161, 1143, 1061, 984, 924, 839 cm−1; MS (ESI) m/z calculated for (C13H12N2O2+H)+ 229, found 229; HRMS (ESI) m/z calculated for (C13H12N2O2+H)+ 229.0978, found 229.0996.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe remaining residue was dissolved in chloroform
  3. washwhich was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-68c8097b1ea049419a9b356038f520ed
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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