Methyl iodide → HCID 57428864, compound

HRID 2267429Notes

Reaction equation

HRID 2267429 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=O)[C:8]([CH3:13])=[CH:9]N(C)C)=[CH:4][CH:3]=1.[NH2:15][C:16]([NH2:18])=[S:17].[CH3:19]C(C)([O-])C.[K+].IC>C(O)(C)C.O1CCCC1>[Br:1][C:2]1[S:6][C:5]([C:7]2[C:8]([CH3:13])=[CH:9][N:18]=[C:16]([S:17][CH3:19])[N:15]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 23665647Potassium tert-butoxideHCID 68463977HCID 68463977, compound

Product 1

HCID 57428864HCID 57428864, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(5-Bromothiophen-2-yl)-3-(dimethylamino)-2-methylprop-2-en-1-one (6.39 g, 23 mmol) was dissolved in isopropyl alcohol (30 mL) at room temperature. Thiourea (1.748 g, 23 mmol) followed by potassium tert-butoxide (23 mL of a 1.0 M solution in tetrahydrofuran) was added to the mixture, which was then heated to reflux overnight. The reaction was cooled to rt and iodomethane (2.86 mL, 46 mmol) was added to the reaction in one portion. The mixture was subsequently stirred for an additional 6 h. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, reduced in vacuo and purified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes to yield a yellow solid (5 g). MS (M+H)+ 302.

Workup

  1. additionwas added to the mixture, which
  2. temperaturewas then heated
  3. temperatureto reflux overnight
  4. customThe volatiles were removed in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium bicarbonate, water and brine
  7. dry with materialThe organic layer was then dried with sodium sulfate
  8. custompurified by column chromatography on silica gel using a gradient of 10 to 40% of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8de9d3192a7b47b9b10f756b2597e0de
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…