2,4,6-Trimethylaniline → HCID 23346511, compound

HRID 1856251Notes

Reaction equation

HRID 1856251 reaction equation
[C:1]1([CH3:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH2:9].C(N([CH2:16][CH3:17])CC)C.BrCC[O:21][S:22](Cl)(=O)=[O:23]>C(OCC)C>[C:1]1([CH3:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][S:22]([CH:16]=[CH2:17])(=[O:23])=[O:21]

Participants

5

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 8471TriethylamineHCID 11770087HCID 11770087, compound

Product 1

HCID 23346511HCID 23346511, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

27.0 g (0.20 mole) mesitylamine were dissolved in 80 ml diethyl ether and mixed with 66.8 g (0.66 mole) triethylamine. The mixture was added dropwise to a stirred solution of 45.6 g (0.22 mole) bromoethylsulphochloride in 160 ml diethyl ether. The mixture was then refluxed for 5.5 hours and evaporated to dryness. The residue was treated with chloroform and 2 N hydrochloric acid and shaken. The chloroform phase was separated and extracted with 2 N sodium hydroxide solution. The alkaline aqueous phase was washed with chloroform, acidified with concentrated hydrochloric acid, and extracted with chloroform. The chloroform phase was dried over anhydrous magnesium sulphate and evaporated to dryness. 15.5 g of the crude title compound was obtained, which, after recrystallization from a mixture of di-isopropylether and hexane, melted at 117°-120° C.

Workup

  1. temperatureThe mixture was then refluxed for 5.5 hours
  2. customevaporated to dryness
  3. additionThe residue was treated with chloroform and 2 N hydrochloric acid
  4. customThe chloroform phase was separated
  5. extractionextracted with 2 N sodium hydroxide solution
  6. washThe alkaline aqueous phase was washed with chloroform
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform phase was dried over anhydrous magnesium sulphate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-cf4b63b2b5b646be91db19d34e454314
Source dataset
uspto-grants-1980_08
Patent number
US04218476

Reaction notes

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