Methanol → 3-Chloro-5-hydroxy-N-isopropyl-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-benzamide

HRID 2268601Notes

Reaction equation

HRID 2268601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:22]C)[CH:21]=1)[C:5]([N:7]([CH:16]([CH3:18])[CH3:17])[CH2:8][CH2:9][C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)=[O:6].B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:5]([N:7]([CH:16]([CH3:17])[CH3:18])[CH2:8][CH2:9][C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 183489363-Chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)ethyl]-benzamide

Product 1

HCID 183488353-Chloro-5-hydroxy-N-isopropyl-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-benzamideYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-benzamide (0.115 g) in anhydrous dichloromethane (5.0 ml) at −78° C. was added 1M boron tribromide solution in dichloromethane (1.36 ml). The reaction mixture was stirred at this temperature for 15 min. The reaction was allowed to warm to room temperature. After 24 h, the reaction was cooled to −78° C. and methanol (1 ml) added. The reaction was allowed to rewarm to room temperature and absorbed on to silica. This was loaded on to an already prepared flash column, eluting with ethyl acetate:petroleum ether (4:1 v/v) and 25:1 dichloromethane:methanol (25:1 v/v) to give the title compound as a white solid (0.072 g).

Workup

  1. waitAfter 24 h
  2. temperaturethe reaction was cooled to −78° C.
  3. customto rewarm to room temperature
  4. customabsorbed on to silica
  5. washeluting with ethyl acetate:petroleum ether (4:1 v/v) and 25:1 dichloromethane:methanol (25:1 v/v)

Sources & evidence

ORD record
ord-944e9167b708430bb565789b804a6562
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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