Trityl chloride → HCID 22726763, compound

HRID 2085984Notes

Reaction equation

HRID 2085984 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[SH:9].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[C:10]1([C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:9][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:3]=2[CH2:2][OH:1])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 22726863HCID 22726863, compound

Product 1

HCID 22726763HCID 22726763, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-hydroxymethyl-3-mercaptopyridine (100 mg, 0.71 mmol) was dissolved in DMF (5 mL) and diisipropylethylamine (0.12 mL, 0.71 mmol) was added followed by triphenylmethylchloride (197 mg, 0.71 mmol). After 30 min. the reaction mixture was partitioned between water and ethyl acetate, and the organic layer was thoroughly washed with water and dried with anhydrous sodium sulfate. Purification by radial chromatography on silica gel produced pure title material (67 mg, 25% yield). 1H NMR (CDCl3) δ 4.17 (s, 2H), 7.20-7.40 (m, 15H), 7.42 (d, 1H, J=6), 8.22 (s, 1H), 8.40 (d, 1H, J=6).

Workup

  1. additiondiisipropylethylamine (0.12 mL, 0.71 mmol) was added
  2. customAfter 30 min. the reaction mixture was partitioned between water and ethyl acetate
  3. washthe organic layer was thoroughly washed with water
  4. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-8742b25efc734a80adb0d47347d1bff5
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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