Hydrochloric Acid → HCID 89767864, compound

HRID 591573Notes

Reaction equation

HRID 591573 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[C:9]2[C:10]([Cl:27])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][C:6]=1[CH3:28].C1COCC1.[OH-].[Na+].Cl>CO>[Cl:27][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:29])=[O:2])=[C:6]([CH3:28])[S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118667068HCID 118667068, compound

Product 1

HCID 89767864HCID 89767864, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl(4-chloro-2-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (132.1 mg), THF (dry) (1.5 mL) and MeOH (1.5 mL) was added 1N NaOH (0.893 mL) at room temperature. The mixture was stirred at 50° C. for 2 h. The mixture was neutralized with 1N HCl. The resulting precipitate was collected by filtration to give a colorless solid. The solid was crystallized from acetone-hexane to give the title compound (87 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customto give a colorless solid
  3. customThe solid was crystallized from acetone-hexane

Sources & evidence

ORD record
ord-46873e96030a42018f522466a873c822
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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