Water → HCID 131716527, compound

HRID 1710229Notes

Reaction equation

HRID 1710229 reaction equation
Cl[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].[S:23](=[O:27])(=[O:26])([OH:25])[OH:24].[OH2:28]>CC(O)C>[S:23]([OH:27])([OH:26])(=[O:25])=[O:24].[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:28])=[O:4])([CH3:22])[CH3:20].[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:24])=[O:4])([CH3:22])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6385Tert-ButylamineHCID 136203604HCID 136203604, compound

Product 1

HCID 131716527HCID 131716527, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

5-(Bromoacetyl)-2-hydroxybenzaldehyde (10g) is suspended in 2-propanol (60ml) under an inert atmosphere and cooled to 0°. To the stirring slurry is added 1,1-dimethylethanamine (13 ml) and the reaction mixture permitted to warm to room temperature and stir for 50 minutes. The solution is then treated with a mixture of concentrated sulfuric acid (3.5ml), 2-propanol (6.5ml) and deionized water (5ml). The reaction mixture is stirred for a further 18 hours whereupon the title compound (10.2g) is isolated by filtration and dried in vacuo at 50°.

Workup

  1. temperaturecooled to 0°

Sources & evidence

ORD record
ord-11ee65ff29504e509d0d470d06ba152f
Source dataset
uspto-grants-1990_08
Patent number
US04952729

Reaction notes

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