Water → HCID 20313828, compound

HRID 2419563Notes

Reaction equation

HRID 2419563 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]1=[N:12][CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.O>COCCOC>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]1=[N:12][CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:29]([C:28]2[CH:32]=[CH:33][C:25]([Cl:24])=[CH:26][CH:27]=2)=[O:30])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 24758Sodium hydrideHCID 12494984HCID 12494984, compound

Product 1

HCID 20313828HCID 20313828, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (57% dispersion in mineral oil; 408 mg) is slurried in 10 ml of anhydrous 1,2-dimethoxyethane and treated dropwise with N-(1,3-benzodithiol-2-ylidene)-1H-indol-3-ethanamine (3g, prepared as described in Example 30) in 15 ml of anhydrous 1,2-dimethoxyethane. The reaction mixture is heated at reflux for 2 hours. A solution of p-chlorobenzoyl chloride (1.69g) in 10 ml of anhydrous 1,2-dimethoxyethane is added dropwise to the refluxing mixture. Refluxing is continued for an additional 4 hours. The reaction mixture is then poured into water (100 ml) and extracted with three 50 ml portions of dichloromethane. The combined dichloromethane extracts are washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel (500 ml) eluting with dichloromethane/pentane (3:2). The fractions containing product with Rf =0.5 (silica gel; dichloromethane) are concentrated in vacuo. The solid thus obtained is recrystallized from hexane/dichloromethane to yield 2.1g of the title compound, melting point 135° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperatureRefluxing
  4. extractionextracted with three 50 ml portions of dichloromethane
  5. washThe combined dichloromethane extracts are washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on silica gel (500 ml)
  9. washeluting with dichloromethane/pentane (3:2)
  10. additionThe fractions containing product with Rf =0.5 (silica gel; dichloromethane)
  11. concentrationare concentrated in vacuo
  12. customThe solid thus obtained
  13. customis recrystallized from hexane/dichloromethane

Sources & evidence

ORD record
ord-203156436df54a1fbb9c31e684478020
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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