Hydrochloric Acid → HCID 22388298, compound

HRID 1072836Notes

Reaction equation

HRID 1072836 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[S:10][C:9]2[C:11]([C:15]([O:17]C)=[O:16])=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[CH2:19][CH3:20])=O.O.NN.[OH-].[K+].Cl>C(O)CO>[C:15]([C:11]1[C:9]2[S:10][C:6]([CH2:4][C:3]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:2]=3[Cl:1])=[C:7]([CH2:19][CH3:20])[C:8]=2[CH:14]=[CH:13][CH:12]=1)([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22388462HCID 22388462, compound

Product 1

HCID 22388298HCID 22388298, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

2-(2,4-Dichlorobenzoyl)-3-ethyl-7-(methoxycarbonyl)benzo[b]thiophene (2.85 g) and hydrazine hydrate (3.50 g) were stirred in ethylene glycol (30 ml) at 160° C. for 1 hr. After cooling, potassium hydroxide (3.30 g) was added, and the mixture was stirred at 160° C. for 2 hr. After cooling, ice and concentrated hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated, and the residue was purified by silica gel column chromatography to give the objective compound (1.98 g) as white crystals.

Workup

  1. temperatureAfter cooling
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eca42d922a6743bc80f7b241067db6fe
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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