Dimethylamine → Hydrochloric Acid

HRID 1729868Notes

Reaction equation

HRID 1729868 reaction equation
[N+](C1N(CCOC(=O)C)C(C2N3N=C([Cl:24])C=CC3=NN=2)=NC=1)([O-])=O.O1CCOCC1.CNC.[N+:34]([C:37]1[N:41]([CH2:42][CH2:43][O:44]C(=O)C)[C:40]([C:48]2[N:52]3[N:53]=[C:54]([N:57]([CH3:59])[CH3:58])[CH:55]=[CH:56][C:51]3=[N:50][N:49]=2)=[N:39][CH:38]=1)([O-:36])=[O:35]>CO>[ClH:24].[N+:34]([C:37]1[N:41]([CH2:42][CH2:43][OH:44])[C:40]([C:48]2[N:52]3[N:53]=[C:54]([N:57]([CH3:59])[CH3:58])[CH:55]=[CH:56][C:51]3=[N:50][N:49]=2)=[N:39][CH:38]=1)([O-:36])=[O:35]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 312751,4-DioxaneHCID 21455917HCID 21455917, compoundHCID 21455979HCID 21455979, compound

Product 2

HCID 313Hydrochloric AcidHCID 21455915HCID 21455915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5 g. crude 3-(5-nitro-1-β-acetoxyethyl-2-imidazolyl)-6-chloro-s-triazolo[ 4,5-b]pyridazine were dissolved in 50 ml. of a mixture of dioxan and methanol (1:1), 5.4 ml. 40 percent aqueous dimethylamine were added thereto, the reaction mixture was stirred for 1 hour at 60° C., evaporated almost completely, the residue triturated with 20 ml. isopropanol, 1.6 g. of solid substance being obtained which has a melting point of 164° - 167° C. After recrystallization thereof from 55 ml. isopropanol, with the addition of charcoal, there was obtained 1 g. 3-(5-nitro-1-β-acetoxyethyl-2-imidazolyl)-6-dimethylamino-s-triazolo [4,3-b]-pyridazine in the form of green-yellow crystals with a melting point of 172° - 174° C. After hydrolysis of 0.4 g. of this substance with 8 ml. 2N hydrochloric acid (90 minutes at 50° C.), the desired compound can be obtained by evaporating the hydrochloric acid solution in a vacuum at 50° C., taking up the residue with 5 ml. water, adjusting to pH 8 - 9 with concentrated aqueous ammonia, filtering off with suction the crystals obtained, washing with water and drying for 2 hours at 120° C. There was thus obtained 0.32 g. 3-(5-nitro-1-β-hydroxyethyl-2-imidazolyl)-6-dimethylamino-s-triazolo [4,3-b]pyridazine, which has a melting point of 220° - 222° C.

Workup

  1. customevaporated almost completely
  2. customthe residue triturated with 20 ml
  3. customof solid substance being obtained which
  4. customAfter recrystallization
  5. additionisopropanol, with the addition of charcoal
  6. customthere was obtained 1 g
  7. customAfter hydrolysis of 0.4 g

Sources & evidence

ORD record
ord-c073ac899b0d4ebfa752f47139958951
Source dataset
uspto-grants-1976_11
Patent number
US03989832

Reaction notes

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