Lawesson's reagent → HCID 58941925, compound

HRID 1845768Notes

Reaction equation

HRID 1845768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=O)[CH:5]=[CH:6][C:7]=1[F:8].COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:38]2)=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[S:38])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58941891HCID 58941891, compound

Product 1

HCID 58941925HCID 58941925, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

A solution of N-(3-chloro-4-fluorophenyl)-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carboxamide (2.3 g, 0.0052 mol) in anhydrous THF (10 mL) was distributed equally into 2 microwave vials. 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (4.2 g, 0.010 mol) (Lawesson's reagent) was added to each vial. The reactions were each heated at 160° C. in a microwave for 15 minutes. The solutions were combined, concentrated and purified by flash chromatography to give the desired product (1.80 g, 76%). MF=C19H27ClFN3OS2Si; LCMS calculated for C19H28ClFN3OS2Si (M+H)+: m/z=460.1.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-36e28f51b61c4e34b79f31fd39161e26
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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