Ethanol → HCID 178510502, compound

HRID 485266Notes

Reaction equation

HRID 485266 reaction equation
[NH2:1]/[C:2](/[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1.S(Cl)(Cl)(=O)=[O:21].C(O)C>ClCCl.ClC(Cl)C>[NH2:1]/[C:2](/[C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1=[O:21]

Participants

6

Reactant 3

HCID 702EthanolHCID 24648Sulfuryl chlorideHCID 178510728HCID 178510728, compound

Product 1

HCID 178510502HCID 178510502, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
-70 °C

Procedure

2.61 gm (9.61 mmols) of (E)-2-[(amino)-4-fluorophenylmethylene]-benzo[b]thiophen-3(2H)-one were dissolved in 50 ml of dichloromethane, the solution was cooled to -70° C, and then a solution of 1.5 gm (11.1 mmols) of sulfuryl chloride in 5 ml of dichloroethane was added dropwise thereto. After 15 hours, 20 ml of 95% ethanol were added, and the reaction mixture was brought to room temperature by removal of the cooling bath. It was then neutralized with aqueous sodium carbonate, the dichloromethane phase was dried with sodium sulfate, the solvent was evaporated in vacuo, and the residue was recrystallized from glacial acetic acid/ethanol (1:4 v/v).

Workup

  1. customthe reaction mixture was brought to room temperature by removal of the cooling bath
  2. dry with materialthe dichloromethane phase was dried with sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was recrystallized from glacial acetic acid/ethanol (1:4 v/v)

Sources & evidence

ORD record
ord-e25b65f2c08e4d8785798f3cb3bf0e97
Source dataset
uspto-grants-1985_08
Patent number
US04536402

Reaction notes

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