Ammonia → HCID 13674823, compound

HRID 1649982Notes

Reaction equation

HRID 1649982 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:14][CH:15](OS(C)(=O)=O)[CH3:16])[S:10]([CH3:13])(=[O:12])=[O:11].[NH3:22]>O.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:14][CH:15]([NH2:22])[CH3:16])[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 13674813HCID 13674813, compound

Product 1

HCID 13674823HCID 13674823, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 1.0 g (3 mmoles) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-methanesulfonyloxy-propane, 10 ml of methanol and 5 ml of concentrated aqueous ammonia is heated at 110° C. for 6 hours in a steel bomb. The mixture is cooled, diluted with 30 ml of water, and methanol is evaporated under reduced pressure. The residue is extracted thrice with 20 ml of chloroform, each. The chloroform solutions are combined, washed thrice with 20 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The residue is triturated with 3 ml of diisopropyl ether. 0.55 g of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-amino-propane are obtained; m.p.: 106°-109° C.

Workup

  1. temperatureThe mixture is cooled
  2. customis evaporated under reduced pressure
  3. extractionThe residue is extracted thrice with 20 ml of chloroform
  4. washwashed thrice with 20 ml of water
  5. dry with materialeach, dried over anhydrous magnesium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is triturated with 3 ml of diisopropyl ether

Sources & evidence

ORD record
ord-d0630904ef4e4a23a7d181e602e7dcba
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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