Diethyl Ether → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062673Notes

Reaction equation

HRID 1062673 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].[NH2:18][C:19]([NH2:21])=[S:20].C(OCC)C>O1CCCC1>[NH2:21][C:19]1[S:20][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:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2723790ThioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

Product 1

HCID 222824852-Amino-4-(3-cyanophenyl)-5-carboethoxythiazoleYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (4.0 g, 13.5 mmol) in 100 mL of tetrahydrofuran was added thiourea (1.03 g, 13.5 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 triturated with ether, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl ether left the title compound as an off-white solid (3.79 g, 98%).

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with ether
  4. washwashed with saturated aq Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a solid

Sources & evidence

ORD record
ord-d19b10cfcc5e4f20aba60ec8af47cc49
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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