HCID 211026, compound → HCID 69438175, compound

HRID 1271714Notes

Reaction equation

HRID 1271714 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH2:8].[I:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](O)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][S:16]([C:13]1[CH:14]=[CH:15][C:10]([I:9])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 211026HCID 211026, compoundHCID 3429171,2-Diaminocyclohexane, cis-

Product 1

HCID 69438175HCID 69438175, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Cis-1,2-diaminocyclohexane (0.70 g, 6.86 mmol) was stirred in CH2Cl2 (40 mL) at 0° C. under N2. A solution of 4-iodobenzenesulfonic acid (0.85 g, 2.81 mmol) in CH2Cl2 (20 mL) was added dropwise to the above solution. It was stirred for 30 min at 0° C. LC/MS showed completion of the reaction. It was washed with 1N HCl. The aqueous solution was basified with 1N NaOH until formation of a cloudy solution. It was extracted with CH2Cl2 (3×), washed with brine, dried (MgSO4), and concentrated to dryness to give cis-N-(2-amino-cyclohexyl)-4-iodobenzenesulfonamide (0.37 g, yield: 35%). 1H NMR (400 MHz, CDCl3) δ 7.86 (d, J=6.8 Hz, 2H), 7.60 (d, J=6.7 Hz, 2H), 3.15 (m, 1H), 2.84 (m, 1H), 1.48 (m, 10H) ppm.

Workup

  1. customcompletion of the reaction
  2. washIt was washed with 1N HCl
  3. extractionIt was extracted with CH2Cl2 (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-421eb0870ed94911aff40ffd4d41b015
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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