Methane → HCID 178424801, compound

HRID 1633259Notes

Reaction equation

HRID 1633259 reaction equation
[ClH:1].Cl.Cl.[NH2:4][C:5]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH:14]([OH:28])[CH2:15][NH:16][CH2:17][CH2:18][NH:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:27].Cl.[CH4:30]>C(O)=O>[ClH:1].[ClH:1].[N:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([O:12][CH2:13][CH:14]([OH:28])[CH2:15][NH:16][CH2:17][CH2:18][NH:19][C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:27])[C:5]=2[NH:4][CH:30]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 20440405HCID 20440405, compound

Product 1

HCID 178424801HCID 178424801, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 21.5 g. 2,3-diamino-1-{2-hydroxy-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propoxy}-benzene trihydrochloride in 150 ml. formic acid is boiled under reflux for 6 hours. After evaporating the reaction mixture in a vacuum, the residue obtained is taken up in 200 ml. 2N hydrochloric acid, boiled under reflux for 4 hours, mixed with active charcoal and filtered while hot. The filtrate is evaporated to dryness and the residue then recrystallized. There are obtained 3.5 g. (17.4% of theory) of the desired compound: m.p. 128°-131° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. customAfter evaporating the reaction mixture in a vacuum
  3. customthe residue obtained
  4. temperatureunder reflux for 4 hours
  5. filtrationfiltered while hot
  6. customThe filtrate is evaporated to dryness
  7. customthe residue then recrystallized
  8. customThere are obtained 3.5 g

Sources & evidence

ORD record
ord-97a37da9d47e446fa3013bbe78eca224
Source dataset
uspto-grants-1984_10
Patent number
US04479962

Reaction notes

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