Cyanamide → HCID 131712146, compound

HRID 443476Notes

Reaction equation

HRID 443476 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH2:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[CH2:17][NH:18][CH2:19][CH3:20])[CH3:7].[CH2:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH:24]1[CH2:32][NH:33][CH2:34][CH3:35])[CH3:22].[N:36]#[C:37][NH2:38]>CC(C)=O>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH2:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[CH2:17][N:18]([CH2:19][CH3:20])[C:37]([NH2:38])=[NH:36])[CH3:7].[CH2:21]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH:24]1[CH2:32][N:33]([CH2:34][CH3:35])[C:37]([NH2:38])=[NH:36])[CH3:22]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 131712147HCID 131712147, compound

Product 1

HCID 131712146HCID 131712146, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 25.3 g of 1-ethyl-2-ethylaminomethylindoline hemisulphate and 25 g of cyanamide is heated at 120° C. for 20 minutes. After cooling, acetone is added and the mixture is filtered. The crystals are taken up in icecold sodium bicarbonate solution and the aqueous phase is extracted with chloroform. The oily base obtained after drying and evaporating the chloroform phase is dissolved in a little methanol and the pH of the solution is adjusted to 6 with sulphuric acid. The solution is evaporated. The residue is triturated with acetone and 1-ethyl-2-(1-ethyl-guanidinomethyl)-indoline hemisulphate is obtained, m.p. 230° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. extractionthe aqueous phase is extracted with chloroform
  4. customThe oily base obtained
  5. customafter drying
  6. customevaporating the chloroform phase
  7. dissolutionis dissolved in a little methanol
  8. customThe solution is evaporated
  9. customThe residue is triturated with acetone

Sources & evidence

ORD record
ord-cb898c2d0ed647ea90dd93a841eed8f3
Source dataset
uspto-grants-1981_04
Patent number
US04260628

Reaction notes

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