Lawesson's reagent → HCID 23130540, compound

HRID 2080173Notes

Reaction equation

HRID 2080173 reaction equation
[NH2:1][C:2]1[N:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:35]2)=CC=1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)=[S:35]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23130367HCID 23130367, compound

Product 1

HCID 23130540HCID 23130540, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-amino-N-(4-benzyloxy-benzyl)-nicotinamide described in Example A-17 (220 mg, 0.67 mmol), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent) (670 mg, 1.7 mmol) and toluene (8 mL) was stirred at 80° C. for 15 minutes, then, refluxed for 45 minutes. After cooling, the precipitate was filtered, and the filtrate was evaporated in vacuo. Purification was carried out by NH silica gel column chromatography (ethyl acetate), and the title compound (28 mg, 0.080 mmol, 12%) was obtained as a pale yellow oil.

Workup

  1. temperaturerefluxed for 45 minutes
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-f19a84bc712b405c826bac1c524c5cf9
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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