Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

Base Information

• Chemical Name: Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester
• CAS No.: 71780-69-3
• Molecular Formula: C₂₆H₃₁NOS
• Molecular Weight: 405.604
• Mol file: 71780-69-3.mol

Synonyms:

Chemical Property of Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester

There total 5 articles about Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester 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:

(+/-)-pentazocine (21820-34-8) → Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester (71780-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 80 deg C, 1 h

2: 11 percent / 0.01 h / 325 °C

3: 1.) LiAlH₄ / 1.) THF, ether, 2 h, 2.) THF, ether, 0.5 h

With lithium aluminium tetrahydride; sodium hydride;

DOI:10.1021/jm00149a020

Reference yield:

Dimethyl-thiocarbamic acid O-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester (89462-04-4) → Thiobenzoic acid S-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester (71780-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 percent / 0.01 h / 325 °C

2: 1.) LiAlH₄ / 1.) THF, ether, 2 h, 2.) THF, ether, 0.5 h

With lithium aluminium tetrahydride;

DOI:10.1021/jm00149a020

Reference yield:

(6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (359-83-1,7313-83-9,7361-76-4,7488-49-5,21820-34-8,39188-58-4,55643-30-6,75257-91-9,146565-86-8) → Thiobenzoic acid S-[(6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester (71780-69-3,83434-64-4,83434-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NaH / dimethylformamide

2: 11 percent / 0.01 h / 325 °C

3: 1.) LiAlH₄

With lithium aluminium tetrahydride; sodium hydride; In N,N-dimethyl-formamide;

upstream raw materials:

benzoyl chloride

(6R,11R)-6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol

(+/-)-pentazocine

Dimethyl-thiocarbamic acid O-[(2R,6R,11R)-6,11-dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl] ester