Hydrochloric Acid → HCID 21964361, compound

HRID 270175Notes

Reaction equation

HRID 270175 reaction equation
[OH-].[Na+].CO.C([O:7][C:8]([C:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)=[CH:13][S:12][C:11]=1[N:23]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:33])=[O:9])C.Cl>O>[Cl:22][C:17]1[CH:16]=[C:15]([C:14]2[C:10]([C:8]([OH:9])=[O:7])=[C:11]([N:23]3[C:24](=[O:33])[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:31]3=[O:32])[S:12][CH:13]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67073891HCID 67073891, compound

Product 1

HCID 21964361HCID 21964361, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of NaOH (1.4 mmol) in a 1:1 mixture of methanol:H2O (6 mL) was added 4-(3,4-dichlorophenyl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-thiophene-3-carboxylic acid ethyl ester (0.7 mmol, Example 6 & 7, Part C). The mixture was heated to reflux for 90 min, then diluted with water (12 mL), chilled in an ice bath, and acidified with concentrated HCl. The product that precipitated was collected by filtration, washed with water, and dried, affording the desired compound as a white solid in 92% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. temperaturechilled in an ice bath
  4. customThe product that precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a1455e375e79402bab09619f25e98b75
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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