Trityl chloride → HCID 618227, compound

HRID 342628Notes

Reaction equation

HRID 342628 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178526856HCID 178526856, compound

Product 1

HCID 618227HCID 618227, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitroimidazole (7.28, g, 64.4 mmol) in 60 mL of dry DMF at 0° C. was added triethylamine (9.87 mL, 70.8 mmol), then chlorotriphenylmethane (17.95 g, 64.4. mmol). After 5 minutes, the solution was warmed to room temperature. After 30 minutes, the reaction mixture was poured over ice, filtered, and washed with ice water. The resulting product was dried in vacuo next to P205 to provide the titled product as a white powder (22.29 g, 97% yield) which was sufficiently pure for use in the next step.

Workup

  1. waitAfter 30 minutes
  2. additionthe reaction mixture was poured over ice
  3. filtrationfiltered
  4. washwashed with ice water
  5. customThe resulting product was dried in vacuo next to P205

Sources & evidence

ORD record
ord-c5ca171444dd452fab159c51ffeb6f35
Source dataset
uspto-grants-1999_01
Patent number
US05859012

Reaction notes

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