Dichloromethane → HCID 178514378, compound

HRID 1949835Notes

Reaction equation

HRID 1949835 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-c45eeb6d8c93441a85cad951219634f5
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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