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3-(Trifluoromethyl)benzoyl chloride → HCID 20085643, compound

HRID 1608814
Notes
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Reaction equation

HRID 1608814 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:24][CH2:25][CH2:26][CH2:27][N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(=[O:23])=[O:22]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[N:28]1([CH2:27][CH2:26][CH2:25][NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=2)(=[O:23])=[O:22])[CH:32]=[CH:31][N:30]=[CH:29]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 15225171HCID 15225171, compound

Product 1

HCID 20085643HCID 20085643, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of 4.24 g (0.0203 mol) of m-trifluoromethylbenzoyl chloride in 10 ml of dichloromethane was added dropwise to a solution of 4.35 g (0.0153 mol) of 2-amino-N-[(3-imidazol-1-yl)propyl]benzenesulfonamide, prepared as in Examples 1A and 1B, in 70 ml of pyridine, under nitrogen. When the reaction was complete, as determined by thin layer chromatography, the resulting reaction mixture was reduced to dryness under reduced pressure. The resultant oil was dissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated, the organic layer was washed with water and again reduced to dryness under reduced pressure to provide an oil. This oil was then purified using column chromatography (8000 ml of a gradient eluent of 0-15% methanol in chloroform). The fractions containing the desired product were combined, reduced to dryness under reduced pressure and then recrystallized from an ethanol/hexane/diethyl ether solution to provide 4.08 g of the desired titled compound (m.p. 145°-147° C.).

Workup

  1. customthe resulting reaction mixture
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with water
  4. customto provide an oil
  5. customThis oil was then purified
  6. additionThe fractions containing the desired product
  7. customrecrystallized from an ethanol/hexane/diethyl ether solution

Sources & evidence

ORD record
ord-f48e3c794d964a71b20704a2248ee5f5
Source dataset
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05397798

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes