2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

Base Information

• Chemical Name: 2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine
• CAS No.: 608537-11-7
• Molecular Formula: C₂₇H₂₉BrN₂O₅S₂
• Molecular Weight: 605.574

Synonyms:2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

Chemical Property of 2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

Chemical Property:

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Technology Process of 2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

There total 5 articles about 2-bromo-N¹,N⁴-bis(3-butenyl)-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 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: 93.0%

1-bromo-4-butene (5162-44-7) + 2-bromo-5-methoxy-N1,N4-bis(phenylsulfonyl)-1,4-phenylenediamine (214119-24-1) → 2-bromo-N1,N4-bis(3-butenyl)-5-methoxy-N1,N4-bis(phenylsulfonyl)-1,4-phenylenediamine (608537-11-7)

Guidance literature:

2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine; With sodium hydride; In tetrahydrofuran; for 0.0833333h; Heating;

1-bromo-4-butene; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 24h; Further stages.; Heating;

DOI:10.1002/ejoc.200300077

Reference yield:

2-methoxy-4-nitrophenylamine (97-52-9) → 2-bromo-N1,N4-bis(3-butenyl)-5-methoxy-N1,N4-bis(phenylsulfonyl)-1,4-phenylenediamine (608537-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / PtO₂*H₂O / dioxane / 16 h / 2250.23 Torr

2.1: 79 percent / pyridine / 3 h / 80 °C

3.1: 95 percent / NBS / tetrahydrofuran / 0.5 h / -78 °C

4.1: NaH / tetrahydrofuran / 0.08 h / Heating

4.2: 93 percent / nBu₄NI / tetrahydrofuran / 24 h / Heating

With pyridine; N-Bromosuccinimide; hydrogen; sodium hydride; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1002/ejoc.200300077

Reference yield:

2-methoxy-1,4-phenylenediamine (5307-02-8) → 2-bromo-N1,N4-bis(3-butenyl)-5-methoxy-N1,N4-bis(phenylsulfonyl)-1,4-phenylenediamine (608537-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / pyridine / 3 h / 80 °C

2.1: 95 percent / NBS / tetrahydrofuran / 0.5 h / -78 °C

3.1: NaH / tetrahydrofuran / 0.08 h / Heating

3.2: 93 percent / nBu₄NI / tetrahydrofuran / 24 h / Heating

With pyridine; N-Bromosuccinimide; sodium hydride; In tetrahydrofuran;

DOI:10.1002/ejoc.200300077

upstream raw materials:

1-bromo-4-butene

2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

2-methoxy-1,4-phenylenediamine

2-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine

Downstream raw materials:

(4RS)-6-[3-butenyl(phenylsulfonyl)amino]-5-iodo-4-iodomethyl-7-methoxy-1-phenylsulfonyl-1,2,3,4-tetrahydroquinoline

6-[3-butenyl(phenylsulfonyl)amino]-5-iodo-7-methoxy-4-methylene-1-phenylsulfonyl-1,2,3,4-tetrahydroquinoline

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