N,N,N',N'-Tetramethylethylenediamine → HCID 13394257, compound

HRID 2164262Notes

Reaction equation

HRID 2164262 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][N:12]([CH3:22])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.CN(C)CCN(C)C.C([Li])CCC.CN(C)S([Cl:41])(=O)=O>O1CCCC1>[Cl:41][C:11]1[N:12]([CH3:22])[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 83372Dimethylsulphamoyl chlorideHCID 20275406HCID 20275406, compoundHCID 178418339Butyllithium

Product 1

HCID 13394257HCID 13394257, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,5-bis(4-methoxyphenyl)-1-methyl-1H-imidazole (10.0 g, 0.034 mol) and N, N, N',N'-tetramethylethylenediamine (three equivalents) in 75 ml of dry tetrahydrofuran was cooled to -78° and treated with n-butyllithium (1.1 equivalents). The mixture was stirred at -78° under nitrogen for one hour and treated with dimethylsulfamoyl chloride (5.5 g, 0.038 mol). The mixture was stirred at -78° for 30 minutes and then overnight at room temperature. The reaction mixture was concentrated in vacuo, and the residue triturated with 10% citric acid. The resulting solid was collected by filtration, washed with water, and dried in vacuo to yield 10.3 g (92%) of the title compound, homogenous by tlc (toluene-ethyl acetate, 6:4; Rf=0.56), m.p. 132°-133°.

Workup

  1. temperaturewas cooled to -78°
  2. stirringThe mixture was stirred at -78° for 30 minutes
  3. customovernight
  4. customat room temperature
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe residue triturated with 10% citric acid
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-eebdea4953454bc9930c97e69cb0acd1
Source dataset
uspto-grants-1985_03
Patent number
US04503065

Reaction notes

Loading…