Sodium Hydroxide → 5-Chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

HRID 505514Notes

Reaction equation

HRID 505514 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=3[N:10]=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:22]N1C(=O)CCC1=O>C1COCC1>[Cl:22][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=3)[N:9]=[N:10][C:11]=2[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 1363439141-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

Product 1

HCID 1361332735-Chloro-1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol (0.984 g, 3.85 mmol) at 0° C. in THF (15 mL) was added 1N NaOH (3.85 mL, 3.85 mmol). The resulting mixture was then stirred for several minutes, after which N-chloro-succinimide (0.515 g, 3.85 mmol) was added in one portion. The stirred reaction mixture was quenched after 5 minutes at 0° C. with aqueous ammonium chloride (25 mL) and extracted with dichloromethane (2×100 mL). The combined extracts were concentrated under reduced pressure. The resulting residue was subjected to reverse phase chromatography (5-95% MeCN/H2O, 0.1% TFA). The product fractions were combined and extracted with dichloromethane (2×100 mL). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product. 1H NMR (DMSO d6) δ 11.61 (s, 1H), 7.44 (d, J=8.5 Hz, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.23 (d, J=8.6 Hz, 1H), 6.90 (d, J=8.8 Hz, 2H), 5.84 (s, 2H), 3.71 (s, 3H).

Workup

  1. customThe stirred reaction mixture
  2. customwas quenched after 5 minutes at 0° C. with aqueous ammonium chloride (25 mL)
  3. extractionextracted with dichloromethane (2×100 mL)
  4. concentrationThe combined extracts were concentrated under reduced pressure
  5. extractionextracted with dichloromethane (2×100 mL)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc34d2e1801c4193adbf28c1b449cad5
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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