(Diethylamino)sulfur trifluoride → HCID 86693333, compound

HRID 575301Notes

Reaction equation

HRID 575301 reaction equation
O[C:2]1([CH3:22])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12.C(N(S(F)(F)[F:29])CC)C>ClCCl>[F:29][C:2]1([CH3:22])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:5]=2[N:4]2[N:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:16]=[C:3]12

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86693330HCID 86693330, compound

Product 1

HCID 86693333HCID 86693333, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-hydroxy-9-iodo-4-methyl-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate (350 mg, 0.85 mmol, 1.00 equiv) in dichloromethane (5 mL) was added diethylaminosulfur trifluoride (271 mg, 1.68 mmol, 2.00 equiv) at 0° C. After being stirred overnight at room temperature the resulting mixture was washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:20) to give 200 mg (57%) of the titled compound as a white solid; LC-MS (ES, m/z) 417 [M+H]+.

Workup

  1. washwas washed with water
  2. extractionextracted with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:20)

Sources & evidence

ORD record
ord-d4728d671dff435d8d85b4e207408c69
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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