5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile

Base Information

• Chemical Name: 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile
• CAS No.: 1258976-18-9
• Molecular Formula: C₁₂H₁₃N₅OS
• Molecular Weight: 275.334

Synonyms:5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile

Chemical Property of 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile

Chemical Property:

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Technology Process of 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile

There total 3 articles about 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile 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: 64.0%

5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]-benzonitrile → 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile (1258976-18-9)

Guidance literature:

With hydrazine hydrate; In isopropyl alcohol; at 100 ℃; for 2h; Product distribution / selectivity; Inert atmosphere;

Reference yield:

3-cyano-4-isopropoxybenzoic acid (258273-31-3) → 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile (1258976-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate / 3 h / 90 °C

2: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 - 70 °C

3: hydrazine hydrate / isopropyl alcohol / 2 h / 100 °C / Inert atmosphere

With tert.-butylnitrite; hydrazine hydrate; copper(ll) bromide; trichlorophosphate; In isopropyl alcohol; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01512

Reference yield:

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (1258440-55-9) → 5-(5-hydrazino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)-oxy]benzonitrile (1258976-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 1 h / 20 - 70 °C

2: hydrazine hydrate / isopropyl alcohol / 2 h / 100 °C / Inert atmosphere

With tert.-butylnitrite; hydrazine hydrate; copper(ll) bromide; In isopropyl alcohol; acetonitrile;

DOI:10.1021/acs.jmedchem.5b01512

upstream raw materials:

3-cyano-4-isopropoxybenzoic acid

5-(5-amino-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile

Downstream raw materials:

1,1-dimethylethyl 2-(5-{3-cyano-4-[(1-methylethyl)oxy]-phenyl}-1,3,4-thiadiazol-2-yl)-3-methyl-2,4,6,7-tetrahydro-5Hpyrazolo[4,3-c]pyridine-5-carboxylate

3-[2-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3-methyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]-pyridin-5-yl]propanoic acid trifluoroacetate

2-[(1-methylethyl)oxy]-5-[5-(3-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-yl]-benzonitrile

tert-butyl 2-(2-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-3-methyl-6,7-dihydro-2H-pyrazolo[4,3-c]pyridin-5(4H)-yl)acetate

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