Hydrochloric Acid → HCID 131715566, compound

HRID 1253324Notes

Reaction equation

HRID 1253324 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[CH2:9][CH2:10][N:11]([C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)[CH2:12][C:13]=1[C:14]=2Cl.[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.C([O-])([O-])=[O:33].[Na+].[Na+]>CO.C(O)C>[OH2:33].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:13](=[CH:12][N:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:30]=3)[C:8]([CH2:9][CH2:10][NH:11][C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)=[N:7][C:6]=2[CH:22]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:13](=[CH:12][N:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:30]=3)[C:8]([CH2:9][CH2:10][NH:11][C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)=[N:7][C:6]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 10340Sodium CarbonateHCID 14156406HCID 14156406, compound

Product 1

HCID 131715566HCID 131715566, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1.5 g (4.53 mmol) of the compound of step B. above, 0.98 mol (9.96 mmol) of phenylhydrazine, 0.75 ml of conc. hydrochloric acid, and 30 ml of absolute ethanol is stirred under reflux for 6 hrs. The cooled precipitate is dissolved in methanol and treated with a Na2CO3 solution. The precipitate which forms is collected, washed with water, and dissolved in hot benzene-hexanes. On cooling the solid is collected. The filtrate, on standing forms a precipitate which is collected and purified by HPLC to furnish 0.788 g (43%) of title compound: m.p. 201°-203° C. (dec.); IR (KBr) 3250, 1585, and 1510 cm-1 ; NMR (DMSO-d6) δ 9.78 (s, 1H), 8.46 (d, 1H), 8.18 (d, 2H), 8.06 (s, 1H), 7.97 (s, 2H), 7.67 (m, 4H), 7.54 (m, 1H), 7.25 (m, 1H), 3.93 (m, 2H), 3.44 (t, 2H).

Workup

  1. temperatureunder reflux for 6 hrs
  2. customThe precipitate which forms is collected
  3. washwashed with water
  4. dissolutiondissolved in hot benzene-hexanes
  5. temperatureOn cooling the solid
  6. customis collected
  7. customis collected
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-b8aaaec85f6749efbc3f3dc096988c6f
Source dataset
uspto-grants-1988_05
Patent number
US04748246

Reaction notes

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