Chlorosulfonic acid → HCID 89761847, compound

HRID 528632Notes

Reaction equation

HRID 528632 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:8]=2[C:9]#[N:10])[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.[Cl:20][S:21](O)(=[O:23])=[O:22]>C(Cl)Cl>[Cl:15][C:12]1[CH:13]=[CH:14][C:7]([N:4]2[CH2:5][CH2:6][O:1][C:2]3[CH:19]=[C:18]([S:21]([Cl:20])(=[O:23])=[O:22])[CH:17]=[CH:16][C:3]2=3)=[C:8]([C:9]#[N:10])[CH:11]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 89761912HCID 89761912, compound

Product 1

HCID 89761847HCID 89761847, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2h-benzo[b][1,4]oxazin-4(3h)-yl)-5-chlorobenzonitrile (480 mg, 1.77 mmol) in DCM (5 mL) was added chlorosulfonic acid (0.47 mL, 7.11 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h. After completion, reaction mixture was poured into ice water (10 mL), quenched with solid sodium bicarbonate (pH˜9-10) and extracted with ethyl acetate (2×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to provide 4-(4-chloro-2-cyanophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonyl chloride (480 mg, 73.3%) as yellow solid. The compound was used in the next step without further purification. LCMS (ESI) m/z: 367.98 (M+H).

Workup

  1. customAfter completion, reaction mixture
  2. customquenched with solid sodium bicarbonate (pH˜9-10)
  3. extractionextracted with ethyl acetate (2×15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4945c736907340d59f5d01fc8c980bcc
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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