Potassium Cyanide → HCID 86693322, compound

HRID 575292Notes

Reaction equation

HRID 575292 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:25]=[CH:24][C:9]2[O:10][CH2:11][CH:12](O)[C:13]3[S:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:15][C:14]=3[C:8]=2[CH:7]=1.C1OCCOCCOCCOCCOCCOC1.[C-:44]#[N:45].[K+]>ClCCl.CC#N.O>[Br:5][C:6]1[CH:25]=[CH:24][C:9]2[O:10][CH2:11][CH:12]([C:44]#[N:45])[C:13]3[S:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:15][C:14]=3[C:8]=2[CH:7]=1

Participants

8

Reactant 4

HCID 9032Potassium CyanideHCID 24386Thionyl ChlorideHCID 2855718-Crown-6HCID 86693321HCID 86693321, compound

Product 1

HCID 86693322HCID 86693322, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (3 mL) was added dropwise to a stirred solution of ethyl 9-bromo-4-hydroxy-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (600 mg, 1.61 mmol, 1.00 equiv) in dichloromethane (10 mL) at 0° C. After being stirred for 4 h at room temperature the resulting mixture was concentrated under vacuum. This resulted in 600 mg (95%) ethyl 9-bromo-4-chloro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate as a yellow solid; LC-MS (ES, m/z) 388, 390 [M+H]+. A suspension this intermediate (600 mg, 1.54 mmol, 1.00 equiv), 18-crown-6 (320 mg, 1.21 mmol, 0.50 equiv) and KCN (524 mg, 8.05 mmol, 5.00 equiv) in CH3CN (10 mL) was stirred overnight at room temperature. The reaction solution was diluted with of 10 mL of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:6) to give 206 mg (35%) of the titled compound as a yellow solid; LC-MS (ES, m/z) 379, 381 [M+H]+

Workup

  1. concentrationwas concentrated under vacuum
  2. customThis resulted in 600 mg (95%) ethyl 9-bromo-4-chloro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate as a yellow solid
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:6)

Sources & evidence

ORD record
ord-0f3c357ac0f647b29de9f8142e26ff4d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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