Trityl chloride → HCID 21880787, compound

HRID 724539Notes

Reaction equation

HRID 724539 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH2:5].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[CH3:1][NH:2][CH2:3][CH2:4][NH:5][C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 8014N-Methylethylenediamine

Product 1

HCID 21880787HCID 21880787, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5 g (67.45 mmol) N1-methyl-ethane-1,2-diamine in 50 mL DMF a solution of 16.72 g (60 mmol) trityl-chloride in 50 mL DMF was added slowly over a period of 10 minutes at room temperature. The mixture was stirred overnight then it was evaporated to dryness, the oil was dissolved in 100 mL ethylacetate, was washed three times with water, dried with sodium sulfate then was evaporated. The components of the oil were separated on a silicagel column using chloroform-methanol gradient elution to give 2.13 g (10%) 197.). 1H-NMR (CDCl3) 7.48–7.44 (m, 6H), 7.27–7.21 (m, 6H), 7.18–7.12 (m, 3H), 3.44 (s, 1H), 2.78–2.74 (m, 2H), 2.42–2.38 (m, 5H).

Workup

  1. customit was evaporated to dryness
  2. dissolutionthe oil was dissolved in 100 mL ethylacetate
  3. washwas washed three times with water
  4. dry with materialdried with sodium sulfate
  5. customthen was evaporated
  6. customThe components of the oil were separated on a silicagel column
  7. washchloroform-methanol gradient elution

Sources & evidence

ORD record
ord-ddfbcb9fd9a644be969cbe41f9cf777f
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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