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Water → 4-Bromo-5-(cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamide

HRID 1844739
Notes
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Reaction equation

HRID 1844739 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH:9]1([CH2:15][C:16]2[N:20]([CH3:21])[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>C1COCC1>[Br:8][C:17]1[CH:18]=[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])[N:20]([CH3:21])[C:16]=1[CH2:15][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 708740515-(Cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamide

Product 1

HCID 867191384-Bromo-5-(cyclohexylmethyl)-1-methyl-1H-pyrrole-2-sulfonamideYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of NBS (68.7 mg, 386 μmol) was added a solution of compound 25e (104 mg, 410 μmol) in THF at −78° C. and stirred for 2 h at −78° C. Water (30 mL) was added and the reaction mixture was extracted with EA (150 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC (hexane/EA=3/1) to give compound 25f (134 mg, 61%).

Workup

  1. extractionthe reaction mixture was extracted with EA (150 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC (hexane/EA=3/1)

Sources & evidence

ORD record
ord-5e4988c72fec42c39b0f3099d8f825d1
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946446B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes