Pivalaldehyde → HCID 18770516, compound

HRID 1920088Notes

Reaction equation

HRID 1920088 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.[CH3:20][C:21]([CH:24]=O)([CH3:23])[CH3:22].CC1C=CC(S(O)(=O)=O)=CC=1.O>>[N:11]1([CH:20]([NH:8][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

5

Reactant 4

HCID 12417PivalaldehydeHCID 696834-BromobenzamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178418385HCID 178418385, compound

Product 1

HCID 18770516HCID 18770516, compound

Procedure

A mixture of 4-bromobenzamide 118 (0.73 g, 3.54 mmol), benzotriazole (0.42 g, 3.52 mmol), pivaldehyde (0.8 mL, 7.27 mmol) and pTSA-HOH (about 60 mg) was heated at reflux for 5 hours in a Dean-Stark apparatus. The mixture was concentrated onto silica gel and purified by chromatography (8:2 CH2Cl2:hexanes to CH2Cl2) to give N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-2,2-dimethylpropyl)-4-bromobenzamide 120 as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours in a Dean-Stark apparatus
  3. concentrationThe mixture was concentrated onto silica gel
  4. custompurified by chromatography (8:2 CH2Cl2:hexanes to CH2Cl2)

Sources & evidence

ORD record
ord-185e59ecd565416985237d99c23504d7
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

Loading…