Lawesson's reagent → HCID 57900186, compound

HRID 628086Notes

Reaction equation

HRID 628086 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=O)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:25]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[S:35])[NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 579001598-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Product 1

HCID 57900186HCID 57900186, compoundYield 116%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (10 g, 0.023 mol) in anhydrous 1,4-dioxane (400 mL) was treated with Lawesson's reagent (7.44 g, 0.018 mol) and heated at 85° C. for 4 h. The orange solution was cooled to room temperature and concentrated in vacuo. The crude product was washed with CH2Cl2 and then dried to give 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbothioamide as a yellow solid (9.41 g, yield 91%). ESI-MS: 449.9.

Workup

  1. temperatureThe orange solution was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. washThe crude product was washed with CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-5caf985ba9254a78b1f6fb69184cc775
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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