Tert-Butylamine → HCID 136061580, compound

HRID 1085998Notes

Reaction equation

HRID 1085998 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=O)=[O:4].[CH3:14][C:15]([CH3:18])([NH2:17])[CH3:16]>CC(O)C>[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:10]=[N:17][C:15]([CH3:18])([CH3:16])[CH3:14])[CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 109446185-(2-Bromoacetyl)-2-hydroxybenzaldehyde

Product 1

HCID 136061580HCID 136061580, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-3 °C

Procedure

5-(Bromoacetyl)-2-hydroxybenzaldehyde (109 g) is suspended in 2-propanol (920 ml) and cooled to -3° C. with stirring. The reaction mixture is treated with 1,1-dimethylethanamine (29.24 g) and stirred at -3° to 0° C. for 30 minutes whereupon precipitation occurs. The reaction mixture is allowed to warm to room temperature, stirred for 90 minutes then cooled to 10° C. and filtered. The solid obtained is washed with ice cold 2-propanol (2×100 ml) and dried in vacuo at 55° C. for 18 hours providing 89 g of 2-bromo-1-[3-[[(1,1-dimethylethyl)imino]methyl]-4-hydroxyphenyl]ethanone.

Workup

  1. stirringstirred at -3° to 0° C. for 30 minutes whereupon precipitation
  2. temperatureto warm to room temperature
  3. stirringstirred for 90 minutes
  4. temperaturethen cooled to 10° C.
  5. filtrationfiltered
  6. customThe solid obtained
  7. washis washed with ice cold 2-propanol (2×100 ml)
  8. customdried in vacuo at 55° C. for 18 hours

Sources & evidence

ORD record
ord-82bed6a4f84243c5b06a64fb8ef6f7a2
Source dataset
uspto-grants-1991_04
Patent number
US05011993

Reaction notes

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