HCID 21273214, compound → HCID 178432766, compound

HRID 1382781Notes

Reaction equation

HRID 1382781 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[N:7]=[C:8]([CH3:21])[N:9](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[CH3:23][N:2]([CH3:1])[C:3](=[O:22])/[CH:4]=[CH:5]/[C:6]1[N:7]=[C:8]([CH3:21])[NH:9][CH:10]=1

Participants

4

Reactant 1

HCID 21273214HCID 21273214, compound

Product 1

HCID 178432766HCID 178432766, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of (E)-N,N-dimethyl-3-[2-methyl-1-(4-methylbenzenesulphonyl)-1H-imidazol-4-yl]-2-propenamide (1.0 g) in pyridine (5 ml) and acetic anhydride (10 ml) was stirred at room temperature for 16 h. The reaction mixture was evaporated in vacuo, methanol (15 ml) was added and stirring was continued for 1 h. The mixture was evaporated in vacuo and the resulting gum partitioned between potassium carbonate solution (ca. 25% saturated) (30 ml) and chloroform (4×25 ml). The combined organic layers were dried, evaporated in vacuo and the residue triturated with ether (30 ml) to give the title compound (340 mg) as a solid, t.l.c. (ether:methanol 9:1), Rf 0.07.

Workup

  1. customThe reaction mixture was evaporated in vacuo, methanol (15 ml)
  2. additionwas added
  3. customThe mixture was evaporated in vacuo
  4. customthe resulting gum partitioned between potassium carbonate solution (ca. 25% saturated) (30 ml) and chloroform (4×25 ml)
  5. customThe combined organic layers were dried
  6. customevaporated in vacuo
  7. customthe residue triturated with ether (30 ml)

Sources & evidence

ORD record
ord-29cdf8df5250429b887834c6e1ddacf4
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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