Hydrochloric Acid → HCID 22388298, compound

HRID 1699857Notes

Reaction equation

HRID 1699857 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-cbaf53f815b1441a9e1c64bcb4ce7247
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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