Trityl chloride → HCID 17961964, compound

HRID 349544Notes

Reaction equation

HRID 349544 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH3:9])[N:5]=[CH:4][C:3]=1[C:10]#[N:11].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH2:7]([N:6]1[C:2]([NH:1][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:3]([C:10]#[N:11])[CH:4]=[N:5]1)[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 10725518HCID 10725518, compound

Product 1

HCID 17961964HCID 17961964, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-amino-1-propyl-1H-pyrazole-4-carbonitrile (16.32 g) in pyridine (160 ml) was added triphenylmethyl chloride (36.35 g) at room temperature. After stirring at 60° C. for 5 hours, the reaction mixture was evaporated in vacuo. The residue was added to a mixture of tetrahydrofuran and brine, and the organic layer was separated and washed with brine. The extract was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. To the residue was triturated with diisopropyl ether to give 1-propyl-5-tritylamino-1H-pyrazole-4-carbonitrile (37.21 g) as a colorless solid.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. additionThe residue was added to a mixture of tetrahydrofuran and brine
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customTo the residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-76e43367873c4362867d928b5f3a2a2b
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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