N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide → 5-(2-Aminopropyl)-2-methoxybenzene-1-sulfonamide

HRID 1869705Notes

Reaction equation

HRID 1869705 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:13][C@H:14]([NH:16]C(=O)C)[CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:4])=[O:3]>Cl>[NH2:16][C@H:14]([CH3:15])[CH2:13][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([S:2]([NH2:1])(=[O:4])=[O:3])[CH:6]=1

Participants

3

Reactant 1

HCID 14099978N-[(2R)-1-(4-Methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide

Product 1

HCID 100603875-(2-Aminopropyl)-2-methoxybenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Intermediate XI (10.5 g) is boiled in 5% HCl (250 ml) under a reflux condenser for 16 to 18 h. The course of the reaction is controlled with TLC detecting the starting substance. After the reaction is complete, the reaction mixture is concentrated to about ⅓ of its volume, then, a saturated solution of sodium carbonate (50 ml) is slowly added dropwise under stirring. After the addition, pH˜10 is controlled and the reaction mixture is stirred for 0.5 hour, then let to crystallize at 0° C. The precipitated crystals are sucked off and the filtrate is concentrated to ½ of its volume and let to crystallize at 0° C. Both fractions (4 g+8 g) of white to brownish crystals are combined and re-crystallized from water. The yield is 7.52 g (80%).

Workup

  1. concentrationthe reaction mixture is concentrated to about ⅓ of its volume
  2. additiona saturated solution of sodium carbonate (50 ml) is slowly added dropwise
  3. additionAfter the addition, pH˜10
  4. stirringthe reaction mixture is stirred for 0.5 hour
  5. customto crystallize at 0° C
  6. concentrationthe filtrate is concentrated
  7. customto crystallize at 0° C
  8. customre-crystallized from water

Sources & evidence

ORD record
ord-92c917812a0e45359dd9ff783f790032
Source dataset
uspto-grants-2009_12
Patent number
US07638649B2

Reaction notes

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