Diethylamine → HCID 13674838, compound

HRID 1649977Notes

Reaction equation

HRID 1649977 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].[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23]>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:14][CH:15]([N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])[CH3:16])[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 13674813HCID 13674813, compound

Product 1

HCID 13674838HCID 13674838, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 15 g (45 mmoles) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-methanesulfonyloxy-propane and 45 ml (31.9 g, 0.44 moles) of diethyl amine is heated at 150° C. for 5 hours in a steel bomb. The mixture is cooled, dissolved in 300 ml of diethyl ether, the solution is washed thrice with 50 ml of water, each, and then extracted thrice with 70 ml of ice-cold 1 n hydrochloric acid, each. The acidic solutions are combined, the traces of diethyl ether are removed under reduced pressure, and then the pH of the solution is adjusted to 9 with concentrated aqueous ammonia. The mixture is allowed to stand at +5° C. for one hour. The separated crystalline substance is filtered off, washed with water and dried. 8.3 g (59.1%) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-diethylamino-propane are obtained as a light beige, crystalline substance; m.p.: 58°-60° C.

Workup

  1. temperatureThe mixture is cooled
  2. washthe solution is washed thrice with 50 ml of water
  3. extractioneach, and then extracted thrice with 70 ml of ice-cold 1 n hydrochloric acid
  4. customthe traces of diethyl ether are removed under reduced pressure
  5. filtrationThe separated crystalline substance is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-82c6db4d0d3e4489932a0fdbdd657328
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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