Triethylamine → perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate

HRID 528644Notes

Reaction equation

HRID 528644 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][C:11]3[CH:15]=[C:16]([S:19](Cl)(=[O:21])=[O:20])[CH:17]=[CH:18][C:10]2=3)=[C:5]([O:23][CH3:24])[CH:4]=1)#[N:2].[F:25][C:26]1[C:31]([OH:32])=[C:30]([F:33])[C:29]([F:34])=[C:28]([F:35])[C:27]=1[F:36].C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][C:11]3[CH:15]=[C:16]([S:19]([O:32][C:31]4[C:30]([F:33])=[C:29]([F:34])[C:28]([F:35])=[C:27]([F:36])[C:26]=4[F:25])(=[O:21])=[O:20])[CH:17]=[CH:18][C:10]2=3)=[C:5]([O:23][CH3:24])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 897620644-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride

Product 1

HCID 89762104perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonateYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (220 mg, 0.603 mmol) in DCM (5 mL) was added pentafluorophenol (110 mg, 0.603 mmol) at 0° C. Triethylamine (0.12 mL, 0.904 mmol) was added at 0° C. and the reaction mixture was stirred at room temperature for 1 h. After completion, the reaction mixture was diluted with DCM (3 mL) and concentrated under reduced pressure. The crude mass thus obtained was purified by column chromatography (12 g column; elution: 5% ethyl acetate in hexane) to get perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (180 mg, 58.4%) as a clear liquid. m/z (ESI) 512.0 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude mass thus obtained
  3. customwas purified by column chromatography (12 g column; elution: 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-eece4c3dabf24a7a87ad191a4ddff306
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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