Chlorosulfonic acid → 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride

HRID 528643Notes

Reaction equation

HRID 528643 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[O:15][CH3:16])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[Cl:21][S:22](O)(=[O:24])=[O:23]>C(Cl)Cl>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:20]=[C:19]([S:22]([Cl:21])(=[O:24])=[O:23])[CH:18]=[CH:17][C:3]2=3)=[C:8]([O:15][CH3:16])[CH:9]=1)#[N:12]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 897616814-(2H-benzo[b][1,4]oxazin-4(3H)-yl)-3-methoxybenzonitrile

Product 1

HCID 897620644-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chlorideYield 20.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2H-benzo[b][1,4]oxazin-4(3H)-yl)-3-methoxybenzonitrile (790 mg, 2.96 mmol) in DCM (10 mL) was added chlorosulfonic acid (0.79 mL, 11.8 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h. After completion, reaction mixture was poured into ice water (15 mL), quenched with solid sodium bicarbonate (pH˜9-10) and the aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layer was dried over sodium sulfate and concentrated to get 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride as a sticky yellow solid (220 mg, 20.3%) which was used without further purification in the next step.

Workup

  1. customAfter completion, reaction mixture
  2. customquenched with solid sodium bicarbonate (pH˜9-10)
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-50e8bd73832c4f52a0d1036772a3c824
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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