Dichloromethane → HCID 178514378, compound

HRID 84572Notes

Reaction equation

HRID 84572 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)=CC=1.C(Cl)Cl.[NH2:51][NH2:52]>O1CCOCC1.CO.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:51][NH2:52])[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

8

Reactant 4

HCID 6344DichloromethaneHCID 9321HydrazineHCID 87949Lawesson's reagentHCID 579001598-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Product 1

HCID 178514378HCID 178514378, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide in dry 1,4-dioxane was added Lawesson's reagent. The 50 mL round-bottom was sealed and heated at 80° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated to give the crude thioamide. The bright yellow crude solid thus obtained was taken up in methanol and methylene chloride and treated with hydrazine. Reaction progress was monitored by LCMS. Upon completion, the mixture was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated to give crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide as a yellow solid.

Workup

  1. customThe 50 mL round-bottom was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customto give the crude thioamide
  5. customThe bright yellow crude solid thus obtained
  6. customReaction progress
  7. extractionextracted with ethyl acetate
  8. washThe combined organics were washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ae54cf9039494cbf973e80a32b78de25
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

Loading…