Methylthiourea → 2-(Methylamino)-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062670Notes

Reaction equation

HRID 1062670 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:18][NH:19][C:20]([NH2:22])=[S:21]>O1CCCC1>[CH3:18][NH:19][C:20]1[S:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[N:22]=1

Participants

4

Reactant 2

HCID 2723704MethylthioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

Product 1

HCID 222824632-(Methylamino)-4-(3-cyanophenyl)-5-carboethoxythiazoleYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (0.65 g, 2.2 mmol) in 20 mL of tetrahydrofuran was added N-methylthiourea (0.20 g, 2.2 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with hexanes/ethyl ether left the title compound as an off-white solid (0.46 g, 73%). MS (ESI) 288.3 (M+H)+.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. washwashed with saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid

Sources & evidence

ORD record
ord-8d02aa7c04fe4e08bf4cbdbd2d5fb687
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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