Cyanuric chloride → HCID 131729745, compound

HRID 215736Notes

Reaction equation

HRID 215736 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].O[CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[C:28]3[CH2:27][C:26]4[C:21](=[CH:22][C:23](=[O:29])[CH2:24][CH:25]=4)[S:20][C:19]=3[CH:18]=[CH:17][C:16]=2[N:30]=1>CN(C=O)C.C(Cl)Cl>[Cl:3][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[C:28]3[CH2:27][C:26]4[C:21](=[CH:22][C:23](=[O:29])[CH2:24][CH:25]=4)[S:20][C:19]=3[CH:18]=[CH:17][C:16]=2[N:30]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 131729746HCID 131729746, compound

Product 1

HCID 131729745HCID 131729745, compoundYield 438.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyanuric chloride (0.29 g, 0.16 mmol) in DMF (1 mL) was stirred for 0.5 hrs, resulting in a white precipitate. Dichloromethane (30 mL) was added, followed by a solution of 3-hydroxymethylpyridothioxanthone (0.25 g, 1.0 mmol) in DCM (20 mL). The solution was stirred at r.t. overnight, then washed with hydrochloric acid (0.5 M, 30 mL) and water, and then dried over sodium sulfate. The mixture was purified by column chromatography on silica gel with DCM/hexane (2:3) as the eluant, yielding 3-chloromethylpyridothioxanthone (0.22 g, 82%). 1H-NMR (CDCl3): 8.88 (1H, d, J 8.4, H1), 8.61 (1H, d, J 8.1, H8), 7.73-7.64 (3H, m, H2+H5+H6), 7.57-7.52 (1H, m, H7), 4.76 (2H, s)). m/z (ES+): 262 [M+H]+, 284 [M+Na]+, 545 [2M+Na]+.

Workup

  1. customresulting in a white precipitate
  2. washwashed with hydrochloric acid (0.5 M, 30 mL) and water
  3. dry with materialdried over sodium sulfate
  4. customThe mixture was purified by column chromatography on silica gel with DCM/hexane (2:3) as the eluant

Sources & evidence

ORD record
ord-f4f7529ba9d444929b44ef3582135a81
Source dataset
uspto-grants-2012_06
Patent number
US08193174B2

Reaction notes

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