Methylamine → HCID 66693763, compound

HRID 1808863Notes

Reaction equation

HRID 1808863 reaction equation
[O:1]1CC(O)O[CH2:3][CH:2]1O.[CH3:9][NH2:10].[N+:11]([CH:13](S(C1C=CC(C)=CC=1)(=O)=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])#[C-:12]>C1COCC1.CN(C=O)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[N:11]=[CH:12][N:10]([CH3:9])[C:3]=1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 186078Glycolaldehyde dimerHCID 27716531-[Isocyano(4-methylbenzene-1-sulfonyl)methyl]-2-methoxybenzene

Product 1

HCID 66693763HCID 66693763, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a soln. of 1,4-dioxane-2,5-diol (120 mg, 0.995 mmol) in THF (8 ml) was added methylamine (2.8 ml, 0.664 mmol) at r.t. The resulting mixture was stirred at r.t for 75 min. Then 1-(isocyano(tosyl)methyl)-2-methoxybenzene (200 mg, 0.664 mmol) was added while keeping reaction mixture at <30° C. by a water bath. The reaction mixture was stirred at r.t overnight. Evaporated to leave white solid, dissolved in DMF, and purified by Pre-HPLC to afford (4-(2-methoxyphenyl)-1-methyl-1H-imidazol-5-yl)methanol (84 mg, 0.377 mmol, 38.6% yield) as a colorless oil. 1H-NMR (MeOD), δ: 8.97 (1H, s), 7.55 (1H, t, J=7.5 Hz), 7.47 (1H, d, J=8.0 Hz), 7.22 (1H, d, 8.0 Hz), 7.15 (1H, t, J=7.5 Hz), 4.67 (2H, s), 4.05 (3H, s), 3.89 (3H, s).

Workup

  1. customreaction mixture at <30° C. by a water bath
  2. stirringThe reaction mixture was stirred at r.t overnight
  3. customEvaporated
  4. customto leave white solid
  5. custompurified by Pre-HPLC

Sources & evidence

ORD record
ord-0834d909f16a4ab8a73428b1e5da29e2
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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