(Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

Base Information

• Chemical Name: (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide
• CAS No.: 136186-29-3
• Molecular Formula: C₁₈H₁₀F₃N₃O₂S
• Molecular Weight: 389.358

Synonyms:(Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

Chemical Property of (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

Chemical Property:

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Technology Process of (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

There total 5 articles about (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

thiophosgene (463-71-8) + α-cyano-β-hydroxy-N-(4-aminophenol)-3-<4-(trifluoromethyl)phenyl>propenamide hydrochloride → (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (136186-29-3)

Guidance literature:

With sodium hydrogencarbonate; In acetone; for 5h; Heating;

DOI:10.1021/jm00115a020

Reference yield:

2-cyano-N-(4-nitrophenyl)acetamide (22208-39-5) → (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (136186-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH (60percent in oil) / 1.) THF, 0 deg C, 15 min, 2.) THF, CH₂Cl₂, 0 deg C, 30 min

2: 92 percent / SnCl₂*2H₂O, conc. HCl / acetic acid / 8 h / 80 °C

3: 63 percent / NaHCO₃ / acetone / 5 h / Heating

With hydrogenchloride; sodium hydride; sodium hydrogencarbonate; tin(ll) chloride; In acetic acid; acetone;

DOI:10.1021/jm00115a020

Reference yield:

4-trifluoromethyl-phenyl acetyl chloride (329-15-7) → (Z)-2-Cyano-3-hydroxy-N-(4-isothiocyanato-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (136186-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH (60percent in oil) / 1.) THF, 0 deg C, 15 min, 2.) THF, CH₂Cl₂, 0 deg C, 30 min

2: 92 percent / SnCl₂*2H₂O, conc. HCl / acetic acid / 8 h / 80 °C

3: 63 percent / NaHCO₃ / acetone / 5 h / Heating

With hydrogenchloride; sodium hydride; sodium hydrogencarbonate; tin(ll) chloride; In acetic acid; acetone;

DOI:10.1021/jm00115a020

upstream raw materials:

thiophosgene

2-cyano-N-(4-nitrophenyl)acetamide

4-trifluoromethyl-phenyl acetyl chloride

(Z)-2-Cyano-3-hydroxy-N-(4-nitro-phenyl)-3-(4-trifluoromethyl-phenyl)-acrylamide

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