Trityl chloride → HCID 44195635, compound

HRID 2368519Notes

Reaction equation

HRID 2368519 reaction equation
[C:1](/[N:4]=[CH:5]/[N:6]([CH3:8])[CH3:7])(=[S:3])[NH2:2].[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[CH3:7][N:6]([CH3:8])/[CH:5]=[N:4]/[C:1](=[S:3])[NH:2][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 9631647[N(E)]-N-[(Dimethylamino)methylene]thiourea

Product 1

HCID 44195635HCID 44195635, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-N′-carbamothioyl-N,N-dimethylformimidamide (63) (5 g, 38 mmol), tritylchloride (11.6 g, 41.8 mmol) and trietheylamine (16 mL, 114 mmol) were refluxed in dichloromethane overnight. The reaction mixture was cooled to room temperature and filtered through a plug of celite. The resulting filtrate was washed with saturated sodium bicarbonate solution, followed with brine. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel column (40%-100% EtOAc in hexanes) to afford (E)-N,N-dimethyl-N′-(tritylcarbamothioyl) formimidamide (64) as a white solid.

Workup

  1. filtrationfiltered through a plug of celite
  2. washThe resulting filtrate was washed with saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel column (40%-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-de829064745f4cba881fb4375232ffb5
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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