Triethylamine → HCID 137175481, compound

HRID 2418477Notes

Reaction equation

HRID 2418477 reaction equation
[OH:1][C:2]1[C:15]([CH2:16][C:17]([NH:19][CH2:20][CH2:21]O)=[O:18])=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]=12.C(N(CC)CC)C.S(Cl)([Cl:36])=O>C(Cl)(Cl)Cl>[OH:1][C:2]1[C:15]([CH2:16][C:17]([NH:19][CH2:20][CH2:21][Cl:36])=[O:18])=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8]3)=[C:4]2[CH:23]=[CH:24][CH:25]=[CH:26][C:3]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 137175482HCID 137175482, compound

Product 1

HCID 137175481HCID 137175481, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1000 mg of 5-hydroxy-N-β-hydroxyethylbenzo[a]phenazine-6-carboxyamide in 30 ml of dry chloroform was added 300 mg of triethylamine, followed by 660 mg of thionyl chloride. The mixture was heated at reflux for 30 minutes and evaporated to dryness under reduced pressure. The residue was dissolved in chloroform, washed with water, dried and the solvent was evaporated. The resulting residue was recrystallized from dimethylformamide to obtain 856 mg (91.8% yield) of 5-hydroxy-N-β-chloroethylbenzo[a]-phenazine-6-carboxyamide as yellow needles, m.p. 183°-186° C., Anal. Calcd. (%) for C19H14N3O2Cl: C, 64.87; H, 4.01; N, 11.94; Found: C, 64.60; H, 4.03; N, 11.66

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. customevaporated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. customthe solvent was evaporated
  8. customThe resulting residue was recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-4b9ee8ad8a1e4b4289d17352963521d4
Source dataset
uspto-grants-1984_09
Patent number
US04472578

Reaction notes

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