Acetohydrazide → HCID 68194502, compound

HRID 2370620Notes

Reaction equation

HRID 2370620 reaction equation
Cl[C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:4](=[O:14])[C:5]2[C:6]([N:13]=1)=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=2.[C:22]([NH:25][NH2:26])(=O)[CH3:23]>C(#N)C>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:3]1[C:4](=[O:14])[C:5]2[C:6](=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[N:13]2[C:22]([CH3:23])=[N:25][N:26]=[C:2]12

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 68194425HCID 68194425, compound

Product 1

HCID 68194502HCID 68194502, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 1B (0.150 g, 0.442 mmol) and acetohydrazide (0.072 g, 0.973 mmol) in acetonitrile (5 mL) was heated at 150° C. for 15 minutes in a Biotage microwave reactor. The solid was filtered. The filtrate was concentrated, treated with saturated aqueous NaHCO3 and extracted with ethyl acetate (2×). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (3:7 to 2:8) to provide the title compound.

Workup

  1. filtrationThe solid was filtered
  2. concentrationThe filtrate was concentrated
  3. additiontreated with saturated aqueous NaHCO3
  4. extractionextracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on a 12 g column
  9. washeluting with CH2Cl2/ethyl acetate (3:7 to 2:8)

Sources & evidence

ORD record
ord-48e492d564b2408fa2ff52e10b66d06d
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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