Lawesson's reagent → HCID 58236986, compound

HRID 1188970Notes

Reaction equation

HRID 1188970 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:14])=O)=[CH:8]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:35])[NH2:14])=[CH:8]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58236996HCID 58236996, compound

Product 1

HCID 58236986HCID 58236986, compoundYield 151.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 7-methoxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (0.73 g) and Lawesson's reagent (0.49 g) in tetrahydrofuran (30 mL) was stirred at 55° C. for 3 h. The reaction mixture was concentrated to give a light yellow oil, which was crystallized from ethyl acetate-hexane to give the title compound (691 mg, 91%) as light yellow prisms. MS 375 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a light yellow oil, which
  3. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-97b5a129e99d49e0b334dd79090534d0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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