HCID 19980025, compound → HCID 19019967, compound

HRID 1461207Notes

Reaction equation

HRID 1461207 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:18]([O-])=O.[Na+].[CH3:22][N:23]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:36])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>Cl.O>[CH2:38]([O:37][C:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][N:23]([C:24]1[CH:29]=[CH:28][C:27]([N:18]=[N:1][C:2]2[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])(=[O:10])=[O:9])=[CH:6][CH:7]=2)=[CH:26][CH:25]=1)[CH3:22])=[O:36])[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 19980025HCID 19980025, compoundHCID 199800346-(4-Aminobenzene-1-sulfonyl)hexan-1-olHCID 23668193Sodium Nitrite

Product 1

HCID 19019967HCID 19019967, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of (4-aminophenyl)-(6-hydroxyhexyl)sulfone (Example 5, 7.2 g, 28 mmol) in 60 mL of 10% HCl was cooled to 0° C. and treated dropwise with 2.1 g (31 mmol) of sodium nitrite in 10 mL of water. The reaction mixture was stirred for 15 minutes and 7.8 g (28 mmol) of butyl N-methyl-N-phenyl-6-aminohexanoate (Example 2) was added slowly. The resulting mixture was gradually warmed to 23° C. and then stirred for 16 hours. The precipitated solid was filtered, washed with water, and air dried. The product was purified by flash chromatography on silica gel, eluting with 20% (v/v) ethyl ether/80% dichloromethane. The eluate was concentrated at reduced pressure and the residue was recrystallized from toluene/heptane to yield 8.1 g (53%) of an orange powder.

Workup

  1. temperatureThe resulting mixture was gradually warmed to 23° C.
  2. stirringstirred for 16 hours
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water, and air
  5. customdried
  6. customThe product was purified by flash chromatography on silica gel
  7. washeluting with 20% (v/v) ethyl ether/80% dichloromethane
  8. concentrationThe eluate was concentrated at reduced pressure
  9. customthe residue was recrystallized from toluene/heptane

Sources & evidence

ORD record
ord-61f5421eee6f4c6d8f33db7073bb5cf7
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

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