2-Methyl-2-butene → 6-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acid

HRID 415752Notes

Reaction equation

HRID 415752 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)([C:13]#[N:14])[CH3:12])[N:9]=2.CC(=CC)C.Cl[O-].[Na+].P([O-])(O)(O)=[O:41].[Na+]>C1COCC1.O.C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:30]([OH:41])=[O:31])[C:5]2[C:6]([CH:29]=1)=[N:7][N:8]([CH2:10][C:11]([C:13]#[N:14])([NH:15][C:16]([C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:21][CH:22]=1)=[O:28])[CH3:12])[N:9]=2

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23665760Sodium HypochloriteHCID 23672064Monosodium phosphateHCID 59327634N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

Product 1

HCID 666203556-chloro-2-[2-cyano-2-({[4-(trifluoromethoxy)phenyl]carbonyl}amino)-propyl]-2H-benzotriazole-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[2-(6-Chloro-4-formyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide (1.5 g) in a mixture of THF (25 mL), t-butanol (10 mL) and 2-methyl-2-butene was added dropwise the solution of sodium hypochlorite (0.9 g) and sodium dihydrogen phosphate (1.15 g) in water (20 mL). After 4 hour at room temperature, the mixture was concentrated under reduced pressure, diluted with water (50 mL) and acidified to pH 2 with normal HCl. The white solid was filtered and washed with water and dried under vacuum to give the title compound (1.35 g, 87%). MS (ES): M/Z [M+H]=468. 1H NMR: (400 MHz, DMSO-d6): 1.72 (s, 3H), 5.48-5.64 (m, 2H), 7.43 (d, J=8.2 Hz, 2H), 7.83 (d, J=2.0 Hz, 1H), 7.99 (d, J=8.8 Hz, 2H), 8.23 (d, J=1.8 Hz, 0H) and 9.41 (br. s, 1H). 19F NMR (376 MHz, DMSO-d6): −57.1 (s, 3F).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. filtrationThe white solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d58b41417665461bb491b514325938ca
Source dataset
uspto-grants-2012_01
Patent number
US08088801B2

Reaction notes

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