Hydrochloric Acid → 2-bromo-N-cyclohexylbenzenesulfonamide

HRID 1523745Notes

Reaction equation

HRID 1523745 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.N1C=CC=CC=1.Cl>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:18][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7965CyclohexylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 33149702-bromo-N-cyclohexylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 20 mL vial were added a stirbar, 2-bromobenzene-1-sulfonyl chloride (1.053 g, 4.12 mmol), cyclohexylamine (431 mg, 4.34 mmol) and dry pyridine (5 mL). The mixture was stirred for 3 hours before adding it to a separatory funnel containing 1 N HCl and EtOAc. The layers were mixed thoroughly and then separated. The organic layer was then washed with water followed by sat. NaHCO3, dried over MgSO4, filtered and evaporated to dryness to give the title compound. MS (ESI): mass calcd. for C12H16NO2SBr 317.01, m/z found 318.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.14 (dd, J=7.9, 1.7, 1H), 7.71 (dd, J=7.9, 1.2, 1H), 7.49-7.42 (m, 1H), 7.42-7.35 (m, 1H), 5.05 (d, J=7.7, 1H), 3.19-3.04 (m, 1H), 1.79-1.66 (m, 2H), 1.66-1.57 (m, 2H), 1.52-1.44 (m, 1H), 1.28-1.04 (m, 5H).

Workup

  1. additionbefore adding it to a separatory funnel
  2. additionThe layers were mixed thoroughly
  3. customseparated
  4. washThe organic layer was then washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-66c176a3ccfd42f28fe3f1daaf5eed78
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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