Phenylthiourea → 2-(Phenylamino)-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062668Notes

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].[C:18]1([NH:24][C:25]([NH2:27])=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([NH:24][C:25]2[S:26][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=3)[N:27]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (0.60 g, 2.03 mmol) in 20 mL of absolute ethanol was added N-phenylthiourea (0.31 g, 2.03 mmol). The resulting mixture was stirred at 80° C. for 3 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 (0.35 g, 49%). MS(NH3—CI) 350 (M+H)+.

Workup

temperatureto cool
customthe solvent was evaporated in vacuo
washwashed with saturated aq NaHCO3 and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto yield a solid

Sources & evidence

ORD record: ord-c0cf73cbacdc4c3e877036933f96a1a3
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06962935B2

Reaction notes

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