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Dimethylamine, hydrochloride → 3-acetyl-N,N-dimethylbenzene-1-sulfonamide

HRID 2210471
Notes
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Reaction equation

HRID 2210471 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:10](F)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Cl.[CH3:15][NH:16][CH3:17].C(N(CC)C(C)C)(C)C>O1CCCC1.Cl>[C:1]([C:4]1[CH:5]=[C:6]([S:10]([N:16]([CH3:17])[CH3:15])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 128213-Acetylbenzenesulfonyl fluorideHCID 81531Diisopropylethylamine

Product 1

HCID 84679503-acetyl-N,N-dimethylbenzene-1-sulfonamideYield 62%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 40.44 g (0.20 mol) of 3-acetylbenzenesulfonyl fluoride in 200 ml of dry tetrahydrofuran is added 20.4 g (0.25 mol) of dimethylamine hydrochloride and 43.6 ml (0.25 mol) of N,N-diisopropylethylamine. The mixture is stirred at room temperature for 48 hours, diluted with 250 ml of 1N HCl and extracted with CH2Cl2. The extract is dried (MgSO4) and the solvent removed. The residue is chromatographed (silica gel column) with CH2Cl2 -hexane (1:1). The fractions containing product are combined, the solvent removed and the residue crystallized from CH2Cl2 -hexane to give 28 g (62%) of white crystals, m.p. 73°-76° C.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe extract is dried (MgSO4)
  3. customthe solvent removed
  4. customThe residue is chromatographed (silica gel column) with CH2Cl2 -hexane (1:1)
  5. additionThe fractions containing product
  6. customthe solvent removed
  7. customthe residue crystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-0fd81e777864411b8b54e97814a5b79e
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05459131

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes