Dipropylamine → 2,6-Bis-(di-n-propylamino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole dihydrochloride

HRID 67107Notes

Reaction equation

HRID 67107 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][C:8]2[C:9](=[CH:11][C:12]3[N:13]=[C:14]([NH:18][C:19](=[O:22])[CH2:20]Cl)[S:15][C:16]=3[CH:17]=2)[N:10]=1)=[O:4].[CH2:23]([NH:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]>O1CCOCC1>[ClH:1].[ClH:1].[CH2:23]([N:26]([N:18]([C:19](=[O:22])[CH3:20])[C:14]1[S:15][C:16]2[C:12](=[CH:11][C:9]3[N:10]=[C:6]([N:5]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:24][CH3:25])[C:3](=[O:4])[CH3:2])[S:7][C:8]=3[CH:17]=2)[N:13]=1)[CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 157546412,6-Bis-(chloroacetyl-amino)benzo[1,2-d:5,4-d']bisthiazole

Product 1

HCID 705475212,6-Bis-(di-n-propylamino-acetylamino)-benzo[1,2-d:5,4-d']bisthiazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7.2 gm of 2,6-bis-(chloroacetyl-amino)-benzo[1,2-d:5,4-d']bisthiazole, 10 gm of di-n-propylamine and 100 ml of dioxane was refluxed for two hours and then evaporated to dryness in vacuo. The residue was dissolved in chloroform, and the solution was washed with water, dried, evaporated to a small volume and chromatographed on a 300 gm silicagel column with chloroform and chloroform/methanol (95:5) as the mobile phase. The title compound, 2.5 gm (25.5% of theory), was eluted, dissolved in chloroform, treated with gaseous hydrogen chloride, and the collected hydrochloride was recrystallized from ethanol/water. M.P. 210° C.

Workup

  1. temperaturewas refluxed for two hours
  2. customevaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution was washed with water
  5. customdried
  6. customevaporated to a small volume
  7. customchromatographed on a 300 gm silicagel column with chloroform and chloroform/methanol (95:5) as the mobile phase
  8. washThe title compound, 2.5 gm (25.5% of theory), was eluted
  9. dissolutiondissolved in chloroform
  10. additiontreated with gaseous hydrogen chloride
  11. customthe collected hydrochloride was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-236f0e59dd9e4b9aa9ece27c11f05b3d
Source dataset
uspto-grants-1982_08
Patent number
US04344946

Reaction notes

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