Dichloromethane → Chloroform ether

HRID 1607708Notes

Reaction equation

HRID 1607708 reaction equation
[C:1](NC1C=C2C(=C(N3CCNCC3)N=1)N=CC=C2)(=[O:3])[CH3:2].[CH2:21](N(CC)CC)[CH3:22].[N+](C1C=CC(C([Cl:37])=O)=CC=1)([O-])=O.[CH2:40]([Cl:42])[Cl:41]>>[CH:40]([Cl:37])([Cl:42])[Cl:41].[CH3:21][CH2:22][O:3][CH2:1][CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 14277727N-[8-(Piperazin-1-yl)-1,7-naphthyridin-6-yl]acetamide

Product 1

HCID 21911965Chloroform etherYield 96.8%

Procedure

To a mixture of 0.24 g of 6-acetamido-8-(1-piperazinyl)-1,7-naphthyridine (Compound No. 1) and 0.1 g of triethylamine added was 15 ml of anhydrous methylene chloride, and the mixture was further added with 0.19 g of p-nitrobenzoyl chloride under ice-cooling, stirred for 3 hour at room temperature, washed with water and dried by anhydrous sodium sulfate. Methylene chloride was distilled off in vacuo, the residue obtained was purified by silica gel column chromatography. Then, 0.36 g of yellowish crystal, 6-acetamido-8-[4-(p-nitrobenzoyl)-1-piperazinyl]-1,7-naphthyridine (Compound No. 8), was obtained by recystallization from chloroform - ether mixed solvent (yield: 96.8%).

Workup

  1. additionadded
  2. temperaturecooling
  3. washwashed with water
  4. dry with materialdried by anhydrous sodium sulfate
  5. distillationMethylene chloride was distilled off in vacuo
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7d4a59dbe3034fa091a19d17a71f00b2
Source dataset
uspto-grants-1989_09
Patent number
US04866176

Reaction notes

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