Tert-Butylamine → HCID 20029894, compound

HRID 325352Notes

Reaction equation

HRID 325352 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]2[O:14][CH2:13]2)[CH:7]=[C:6]([Cl:15])[C:3]=1[CH:4]=[O:5].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]([OH:14])[CH2:13][NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[C:6]([Cl:15])[C:3]=1[CH:4]=[O:5]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 20029869HCID 20029869, compound

Product 1

HCID 20029894HCID 20029894, compound

Procedure

A mixture of 2,6-dichloro-4-(2,3-epoxypropoxy)benzaldehyde (3 gm) and tert-butylamine (20 ml) is heated at 45° for 17 hours. The excess tert-butylamine is removed under reduced pressure (20 mm). The oil is dissolved in 6 N hydrochloric acid (25 ml) and heated for 1 hour. The acid solution is added to boiling saturated aqueous sodium carbonate with nitrogen ebullition. The basic solution is extracted with chloroform. The chloroform is dried over anhydrous sodium sulfate, filtered and concentrated to 2,6-dichloro-4-(3-tert-butylamino-2-hydroxypropoxy)benzaldehyde which is used without further purification.

Workup

  1. temperatureis heated at 45° for 17 hours
  2. customThe excess tert-butylamine is removed under reduced pressure (20 mm)
  3. dissolutionThe oil is dissolved in 6 N hydrochloric acid (25 ml)
  4. temperatureheated for 1 hour
  5. additionThe acid solution is added
  6. extractionThe basic solution is extracted with chloroform
  7. dry with materialThe chloroform is dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to 2,6-dichloro-4-(3-tert-butylamino-2-hydroxypropoxy)benzaldehyde which
  10. customis used without further purification

Sources & evidence

ORD record
ord-884628990cd2437fa75d0b2827fd34c9
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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