Hydrochloric Acid → HCID 178527939, compound

HRID 452593Notes

Reaction equation

HRID 452593 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:12][NH2:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:14](=S)=[S:15].C(N(CC)CC)C.Cl>C(O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:11][C:14]([SH:15])=[N:13][N:12]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 433489731H-Indazole-5-carbohydrazide

Product 1

HCID 178527939HCID 178527939, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 1H-indazole-5-carbohydrazide (4.40 g, 25.0 mmol), carbon disulfide (3.76 mL, 62.5 mmol) and triethylamine (4.18 mL, 30.0 mmol) in ethanol (100 mL) was heated under reflux for 7 hr. After cooling, the reaction mixture was poured into water, and acidified with 1M hydrochloric acid. The precipitate was collected by filtration, dried and recrystallized from tetrahydrofuran to give the title compound (5.27 g, yield 97%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hr
  3. temperatureAfter cooling
  4. filtrationThe precipitate was collected by filtration
  5. customdried
  6. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-d241b49365cd44fe94ea2c14f8cb0715
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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