Dichloromethane → HCID 19913991, compound

HRID 1090840Notes

Reaction equation

HRID 1090840 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[N:6]=[N:7][C:8]([NH:11][N:12]=[C:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:22][CH2:23][NH2:24].C(OC(C)C)(C)C.[Cl:37]CCl>>[ClH:37].[ClH:37].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:22][CH2:23][NH:24][CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]2[N:6]=[N:7][C:8]([NH:11][N:12]=[C:13]([CH3:15])[CH3:14])=[CH:9][CH:10]=2)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7914Diisopropyl EtherHCID 8421HomoveratrylamineHCID 15020497HCID 15020497, compound

Product 1

HCID 19913991HCID 19913991, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(2,3-epoxypropoxy)-6-isopropylidenehydrazinopyridazine (20 g) and 3,4-dimethoxyphenethylamine (40 ml) was stirred at 50° C for 4 hours. After cooling, the mixture was dissolved in dichloromethane (100 ml) and poured into diisopropyl ether (800 ml). After stirring for 1 hour the precipitate was collected and triturated with diisopropyl ether (400 ml). The collected solid was dissolved in ethanol (300 ml) and 5.4N hydrochloric acid (35 ml) Was added dropwise. The solvent was evaporated under vacuum, the residue was diluted with acetone (100 ml) and toluene (100 ml) and evaporated to dryness The residue was crystallised from ethanolacetone to afford 26.6 g of the title compound as a pale yellow solid. m.p. 206°-209° C. (with decomposition).

Workup

  1. temperatureAfter cooling
  2. stirringAfter stirring for 1 hour the precipitate
  3. customwas collected
  4. customtriturated with diisopropyl ether (400 ml)
  5. dissolutionThe collected solid was dissolved in ethanol (300 ml)
  6. addition5.4N hydrochloric acid (35 ml) Was added dropwise
  7. customThe solvent was evaporated under vacuum
  8. additionthe residue was diluted with acetone (100 ml) and toluene (100 ml)
  9. customevaporated to dryness The residue
  10. customwas crystallised from ethanolacetone

Sources & evidence

ORD record
ord-8e87b3609c8f4c1d9ac9852129f426d0
Source dataset
uspto-grants-1992_01
Patent number
US05082939

Reaction notes

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