Trityl chloride → HCID 68461570, compound

HRID 503021Notes

Reaction equation

HRID 503021 reaction equation
[NH:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[C:19](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:20]1([C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:4]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11])=[N:1][N:2]=[N:3]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178510971HCID 178510971, compound

Product 1

HCID 68461570HCID 68461570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1H-tetrazole-5-pentanenitrile (30 g, 198 mmol) in a mixture of methylene chloride (200 mL) and triethylamine (30 mL, 218 mmol) was stirred as trityl chloride (61 g, 218 mmol) was added. After 16 h, the reaction was treated with an aqueous solution of sodium bicarbonate and extracted with methylene chloride. The combined organic layers were dried and concentrated. The residue was dissolved in ether and hexane was added. The resulting solid was isolated by filtration to give 1-(triphenylmethyl)-1H-tetrazole-5-pentanenitrile as a white solid.

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ether
  6. additionhexane was added
  7. customThe resulting solid was isolated by filtration

Sources & evidence

ORD record
ord-be65b21c7588408ab44e975170cdbbac
Source dataset
uspto-grants-2010_08
Patent number
US07776896B2

Reaction notes

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