8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

Base Information

Chemical Name:8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide
CAS No.:1189811-55-9
Molecular Formula:C₂₁H₁₈ClNO₃S
Molecular Weight:399.898
Hs Code.:

Synonyms:8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

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Chemical Property of 8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

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Technology Process of 8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

There total 10 articles about 8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide 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: 48.9%

: 1189810-56-7
2-[(2-chlorophenyl)methylcarbamoyl]-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-8-carboxylic acid methyl ester

: 1189811-55-9
8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

Guidance literature:: 2-[(2-chlorophenyl)methylcarbamoyl]-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-8-carboxylic acid methyl ester; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran;

Reference yield:

: 157245-84-6
ethyl 4-(3-bromophenoxy)butanoate

: 1189811-55-9
8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

Guidance literature:: Multi-step reaction with 9 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 48 h / 50 °C

2: polyphosphoric acid; celite / toluene / 5 h / 110 °C

3: N,N-dimethyl-formamide / 20 °C

4: potassium carbonate / N,N-dimethyl-formamide / 50 °C

5: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 50 °C

6: thionyl chloride / 2 h / 80 °C

7: triethylamine / dichloromethane / 0 - 20 °C

8: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 48 h / 70 °C / 2585.81 Torr

9: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; lithium aluminium tetrahydride; thionyl chloride; lithium hydroxide monohydrate; water; palladium diacetate; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm2007084

Reference yield:

: 1189815-76-6
methyl 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylate

: 1189811-55-9
8-hydroxymethyl-4,5-dihydro-6-oxa-1-thiabenzo[e]azulene-2-carboxylic acid (2-chlorophenyl)methylamide

Guidance literature:: Multi-step reaction with 5 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 50 °C

2: thionyl chloride / 2 h / 80 °C

3: triethylamine / dichloromethane / 0 - 20 °C

4: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 48 h / 70 °C / 2585.81 Torr

5: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; lithium aluminium tetrahydride; thionyl chloride; lithium hydroxide monohydrate; water; palladium diacetate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm2007084