Water → beta-Dimethylamino-alpha-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone hydrochloride

HRID 845168Notes

Reaction equation

HRID 845168 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([NH:19][N:20]=[C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:22]([CH3:27])[CH2:23][N:24]([CH3:26])[CH3:25])(=[O:18])=[O:17])([CH3:3])[CH3:2].C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN)(=O)=O)(C)C.[ClH:54].CC(CN(C)C)C(C1C=CC=CC=1)=O.O>C(Cl)Cl.C(O)(=O)C>[ClH:54].[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:7]=[C:6]([CH:13]([CH3:14])[CH3:15])[C:5]=1[S:16]([NH:19][N:20]=[C:21]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:22]([CH3:27])[CH2:23][N:24]([CH3:25])[CH3:26])(=[O:18])=[O:17])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 1999923-(Dimethylamino)-2-methylpropiophenone hydrochlorideHCID 3593332,4,6-TriisopropylbenzenesulphonohydrazideHCID 86741736beta-Dimethylamino-alpha-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone

Product 1

HCID 86741737beta-Dimethylamino-alpha-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

β-Dimethylamino-α-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone can be prepared as follows: 2,4,6-triisopropylbenzenesulphonylhydrazine (23.8 g) is added to α-methyl-β-dimethylaminopropiophenone hydrochloride (16.3 g) dissolved in methylene chloride (150 cc) and acetic acid (5 cc). The solution is stirred at ambient temperature for 24 hours and is then poured into water (50 cc). The aqueous phase is extracted with methylene chloride (2×50 cc) and then the organic phases are combined, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (2.7 kPa) at 40° C. to give a yellow oil which is crystallised in a mixture (120 cc) of ethyl acetate and isopropyl ether (50/50 by volume). In this way β-dimethylamino-α-methylpropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone hydrochloride (16 g) is obtained in the form of a white solid melting at 147° C.

Workup

  1. extractionThe aqueous phase is extracted with methylene chloride (2×50 cc)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure (2.7 kPa) at 40° C.
  5. customto give a yellow oil which
  6. customis crystallised in a mixture (120 cc) of ethyl acetate and isopropyl ether (50/50 by volume)

Sources & evidence

ORD record
ord-b7e1fd274eea4215aee66863b0f7e084
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

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