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Dimethylamine → 2-(4-Tert-butyl-benzenesulfonylamino)-5-chlorobenzoyl chloride

HRID 1692124
Notes
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Reaction equation

HRID 1692124 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:27]=[C:26](F)[C:25]([Cl:29])=[CH:24][C:20]=2[C:21]([OH:23])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].CNC.C[N-]C>C1COCC1.CCCCCC>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:27]=[CH:26][C:25]([Cl:29])=[CH:24][C:20]=2[C:21]([Cl:3])=[O:23])(=[O:17])=[O:16])=[CH:11][CH:10]=1)([CH3:7])([CH3:8])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 182180DimethylazanideHCID 593030312-(4-Tert-butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid

Product 1

HCID 866183462-(4-Tert-butyl-benzenesulfonylamino)-5-chlorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Procedure

Thionyl chloride (220 mL, 3.02 mol) was introduced to a 1 L round bottom flask fitted with a magnetic stir bar. 2-(4-tert-Butyl-benzenesulfonylamino)-5-chloro-4-fluoro-benzoic acid (22 g, 57.0 mmol) was added under rapid agitation and the mixture was heated at reflux under a nitrogen atmosphere. The reaction progress was monitored by the addition of a few drops of the reaction mixture into ˜1 mL of 2.0 M dimethylamine in THF, followed by LCMS analysis. Complete conversion to the dimethyl amide was observed at 1.25 h. The crude mixture was subsequently concentrated in vacuo to produce an orange oil. Hexane (50 mL) was added to the flask and the mixture concentrated again to afford 2-(4-tert-butyl-benzenesulfonylamino)-5-chloro-benzoyl chloride as an orange crystalline solid which was utilized direction in the next step.

Workup

  1. customfitted with a magnetic stir bar
  2. temperaturethe mixture was heated
  3. temperatureat reflux under a nitrogen atmosphere
  4. concentrationThe crude mixture was subsequently concentrated in vacuo
  5. customto produce an orange oil
  6. concentrationthe mixture concentrated again

Sources & evidence

ORD record
ord-46938bff222743bab672f7dfbb2f4636
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153818B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes