Lithium Hydroxide → HCID 2812576, compound

HRID 2170832Notes

Reaction equation

HRID 2170832 reaction equation
[Li+].[OH-].Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26]>O.CCOCC.C(OCC)(=O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][C:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)=[O:26])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 2812576HCID 2812576, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of LiOH (2.4 g) in 50 mL water was added to a suspension of 1-(4-chloro-phenyl)hydrazine HCl salt (17.9 g, 100 mmol) in Et2O (300 mL), and the resulting mixture was stirred for 30 minutes. After the mixture became homogenous, the organic layer was separated, and triethylamine (1 eq.) followed by thiophene-2-carbonyl chloride (14.6 g, 100 mmol) were added slowly dropwise at a constant temperature of 0° C. The mixture was stirred for additional 1 hour at room temperature, and then the organic layer was diluted with ethyl acetate (100 mL), washed with brine, and dried over Na2SO4. The crude N′-(4-chlorophenyl)thiophene-2-carbohydrazide (24 g) obtained after the removal of the solvent was used in the next step without further purification.

Workup

  1. customthe organic layer was separated
  2. additionwere added slowly dropwise at a constant temperature of 0° C
  3. stirringThe mixture was stirred for additional 1 hour at room temperature
  4. washwashed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-7141e9298ee5403bb32a03972f8bddf4
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

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