Hydrochloric Acid → HCID 14822571, compound

HRID 1085999Notes

Reaction equation

HRID 1085999 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]=NC(C)(C)C)[CH:6]=1)=[O:4].[CH3:18][C:19]([CH3:22])([NH2:21])[CH3:20].Cl.CC([OH:27])C>>[ClH:1].[CH3:18][C:19]([NH:21][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:6]=1)[CH:12]=[O:27])=[O:4])([CH3:22])[CH3:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3776Isopropanol2×HCID 6385Tert-ButylamineHCID 136203604HCID 136203604, compound

Product 1

HCID 14822571HCID 14822571, compound

Procedure

2-Chloro-1-[3-[[(1,1-dimethylethyl)imino]methyl]-4-hydroxyphenyl]ethanone (10 g) is suspended in 2-propanol (60 ml) with stirring at room temperature under an inert atmosphere. This slurry is treated with 1,1-dimethylethanamine (16.4 ml) and heated at reflux for 1 hour then treated with a mixture of 12M hydrochloric acid (13.0 ml) and 2-propanol (20 ml). The reaction mixture is allowed to cool to room temperature and stir for an additional 18 hours. Filtration of the reaction mixture affords (6.2 g) of 5-[[(1,1-dimethylethyl) amino]acetyl]-2-hydroxybenzaldehyde hydrochloride after washing with diethylether (50 ml) and drying in vacuo at 50°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool to room temperature
  4. stirringstir for an additional 18 hours
  5. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-bc49e96436194c8c84042a3f7d6062f0
Source dataset
uspto-grants-1991_04
Patent number
US05011993

Reaction notes

Loading…