Water → HCID 20313829, compound

HRID 2419562Notes

Reaction equation

HRID 2419562 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.[CH:24]1[C:29]([CH2:30]Cl)=[CH:28][CH:27]=[C:26]([Cl:32])[CH:25]=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]([CH2:30][C:29]2[CH:28]=[CH:27][C:26]([Cl:32])=[CH:25][CH:24]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 12494984HCID 12494984, compound

Product 1

HCID 20313829HCID 20313829, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Sodium hydride (50% dispersion in mineral oil; 155 mg) is slurried in 5 ml of anhydrous 1,2-dimethoxyethane and treated dropwise with N-(1,3-benzodithiol-2-ylidene)-1H-indol-3-ethanamine (1g, prepared as described in Example 30) in 5 ml of anhydrous 1,2-dimethoxyethane. The mixture is heated at reflux for 3 hours. A solution of α,p-dichlorotoluene (520 mg) in 5 ml of anhydrous 1,2-dimethoxyethane is added dropwise to the refluxing reaction mixture. Refluxing is continued for four hours after addition is complete. The reaction mixture is then poured into water (50 ml) and extracted with two 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 resultant solid is chromatographed on silica gel (200 ml) eluting with dichloromethanepentane (1:1). The fractions containing product with Rf =0.8 (silica gel, dichloromethane) are concentrated. The solid thus obtained is recrystallized from hexane to yield 600 mg of the title compound, melting point 120°-121° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperatureRefluxing
  4. additionafter addition
  5. extractionextracted with two 50 ml portions of dichloromethane
  6. washThe combined dichloromethane extracts are washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resultant solid is chromatographed on silica gel (200 ml)
  10. washeluting with dichloromethanepentane (1:1)
  11. additionThe fractions containing product with Rf =0.8 (silica gel, dichloromethane)
  12. concentrationare concentrated
  13. customThe solid thus obtained
  14. customis recrystallized from hexane

Sources & evidence

ORD record
ord-59d7c1821f3e44968baa8f30e20a206a
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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