Hydrochloric Acid → HCID 14156410, compound

HRID 1253320Notes

Reaction equation

HRID 1253320 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[N:17]=[C:16]4[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:15]4=[C:14](Cl)[C:13]=3[CH2:12]2)=[CH:7][CH:6]=1)[CH3:2].[C:28]1([NH:34][NH2:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>CO.CCOCC.C(O)C>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:20][CH2:19][C:18]2[C:13]3=[CH:12][N:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:35]=[C:14]3[C:15]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:16]=3[N:17]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 10340Sodium CarbonateHCID 14156402HCID 14156402, compound

Product 1

HCID 14156410HCID 14156410, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1 g (2.5 mmol) of the compound of step C. above, 0.539 ml (5.48 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 is collected and washed with water to yield 0.388 of a brown solid. Trituration with ether affords 0.303 g (26%) of the title compound as a light brown solid: m.p. 170°-172° C.; IR (KBr) 3320, 1687, and 1604 cm-1 ; NMR (DMSO-d6) δ 9.56 (s, 1H), 8.27 (d, 1H), 8.17 (d, 2H), 8.07 (s, 1H), 7.70 (m, 5H), 7.54 (t, 1H), 6.70 (d, 2H), 4.23 (q, 2H), 3.78 (m, 2H), 3.46 (t, 2H), 1.26 (t, 3H).

Workup

  1. temperatureunder reflux for 6 hrs
  2. customThe precipitate is collected
  3. washwashed with water
  4. customto yield 0.388 of a brown solid

Sources & evidence

ORD record
ord-5abf6ab4ad384a4085bf89b657a8d4c5
Source dataset
uspto-grants-1988_05
Patent number
US04748246

Reaction notes

Loading…