2,4-Dimethoxybenzylamine → HCID 68291850, compound

HRID 339826Notes

Reaction equation

HRID 339826 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][S:16](Cl)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][S:16]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:22]=2[O:21][CH3:20])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 86705294HCID 86705294, compound

Product 1

HCID 68291850HCID 68291850, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under inert gas, 4.89 g of (4-benzyloxyphenyl)methanesulfonyl chloride were initially charged in 120 ml of THF, then, at a temperature of −20° C., 6.10 ml of 2,4-dimethoxybenzylamine were added dropwise and the reaction solution was allowed to come to 0° C. within 30 minutes. The reaction solution was diluted with 150 ml of ethyl acetate and washed with water, dilute aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined, concentrated by rotary evaporation and dried under high vacuum. This gave the product (3.23 g) with a molecular weight of 427.5 g/mol (C23H25NO5S).

Workup

  1. washwashed with water, dilute aqueous potassium hydrogensulfate solution, saturated aqueous sodium hydrogencarbonate solution and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe crude product was purified by means of normal phase chromatography
  5. concentrationconcentrated by rotary evaporation
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-478b64e360a64913a5a3eebf548380c3
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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