Acetic Acid → HCID 20070367, compound

HRID 981526Notes

Reaction equation

HRID 981526 reaction equation
[CH3:1][C:2]([NH:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])([CH3:5])[CH2:3][OH:4].Cl.N.[C:16](O)(=O)[CH3:17]>>[CH3:16][C:17]1[N:6]([C:2]([CH3:1])([CH3:5])[CH2:3][OH:4])[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 119615571-Propanol, 2-[(2-aminophenyl)amino]-2-methyl-

Product 1

HCID 20070367HCID 20070367, compound

Procedure

A mixture of 2-(1,1-dimethyl-2-hydroxyethyl)aminoaniline (from Preparation 2(a)) (8.4 g), acetic acid [4.2 g], and 4N hydrochloric acid [50 ml] were refluxed for 30 hours. The reaction was cooled and neutralised with concentrated aqueous ammonia. The solution was extracted with a mixture of tetrahydrofuran (1 part) and dichloromethane (3 parts) (3×100 ml). The organic phases were combined, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was recrystallised from ethyl acetate yielding the title compound as a white solid 3.8 g (40%), m.p. 180°-181° C.

Workup

  1. temperaturewere refluxed for 30 hours
  2. temperatureThe reaction was cooled
  3. extractionThe solution was extracted with a mixture of tetrahydrofuran (1 part) and dichloromethane (3 parts) (3×100 ml)
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was recrystallised from ethyl acetate yielding the title compound as a white solid 3.8 g (40%), m.p. 180°-181° C.

Sources & evidence

ORD record
ord-16935e55514c43b79f4559b00bf88107
Source dataset
uspto-grants-1991_02
Patent number
US04992447

Reaction notes

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