Dichloromethane → HCID 67054864, compound

HRID 241390Notes

Reaction equation

HRID 241390 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:22]=[CH:21][C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[CH:15][C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25](CO)[N:24]=3)=[N:13]4)[N:10]=2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.S(Cl)([Cl:40])=O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:48]([Cl:50])Cl>>[Cl:40][CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:22]=[CH:21][C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[CH:15][C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:48][Cl:50])[N:24]=3)=[N:13]4)[N:10]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 67054820HCID 67054820, compound

Product 1

HCID 67054864HCID 67054864, compoundYield 64%

Procedure

Under a stream of argon, compound (21) (0.7 g; 1.77 mmol) was suspended in methylene chloride (15 mL) in an ice bath. To the reaction mixture, triethylamine (0.54 g; 5.32 mmol) and thionyl chloride (0.51 g; 4.25 mmol) were sequentially added. The resulting reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was made alkaline with a 5% aqueous sodium carbonate, and then evaporated under reduced pressure. The resulting residue was dissolved in chloroform/methanol=3/1, and inorganic matters were removed by membrane filtration. The filtrate was evaporated under reduced pressure to give a residue, and the resulting residue was separated and purified by silica gel column chromatography (SiO2, 200 g) (chloroform/methanol=10/1 to 5/1 to 3/1) to give 0.49 g (yield: 64%) of the title compound (22).

Workup

  1. customThe resulting reaction mixture
  2. customevaporated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in chloroform/methanol=3/1, and inorganic matters
  4. customwere removed by membrane filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give a residue
  7. customthe resulting residue was separated
  8. custompurified by silica gel column chromatography (SiO2, 200 g) (chloroform/methanol=10/1 to 5/1 to 3/1)

Sources & evidence

ORD record
ord-fc82644a25fa4ab9974dc3196e690a15
Source dataset
uspto-grants-2014_02
Patent number
US08648194B2

Reaction notes

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