4-Nitrobenzenesulfonyl chloride → HCID 12669330, compound

HRID 223238Notes

Reaction equation

HRID 223238 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:19][CH3:20])=[CH:5][C:6]2[CH:12]([CH2:13][O:14][CH2:15][CH2:16][OH:17])[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:18]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22]>C(N(CC)CC)C>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([O:17][CH2:16][CH2:15][O:14][CH2:13][CH:12]2[C:6]3[CH:5]=[C:4]([O:19][CH3:20])[C:3]([O:2][CH3:1])=[CH:18][C:7]=3[CH2:8][CH2:9][CH2:10][O:11]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chloride2×HCID 12669329HCID 12669329, compound

Product 1

HCID 12669330HCID 12669330, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To a mixture of 3.00 g (10.6 mmoles) of 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethanol and 1.63 ml (11.7 mmoles) of triethylamine is added 2.59 g (11.7 mmoles) of p-nitrobenzenesulfonyl chloride. The reaction mixture is stirred at room temperature for 1 hour and then heated at 50° for 30 minutes. To this is added an additional 0.5 g of p-nitrobenzenesulfonyl chloride and 0.5 ml of triethylamine. After stirring at room temperature for 30 minutes, the reaction mixture is extracted with aqueous sodium bicarbonate and brine. The organic layer is filtered through sodium sulfate and taken to dryness. The residue is chromatographed on silica gel using 1% methanol methylene chloride as eluant to give 1.56 g (32%) 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzoxepin-1-yl)methoxy]ethyl 4-nitrobenzene sulfonate. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperatureheated at 50° for 30 minutes
  2. stirringAfter stirring at room temperature for 30 minutes
  3. extractionthe reaction mixture is extracted with aqueous sodium bicarbonate and brine
  4. filtrationThe organic layer is filtered through sodium sulfate
  5. customThe residue is chromatographed on silica gel using 1% methanol methylene chloride as eluant

Sources & evidence

ORD record
ord-abac392004e94307ba5509ef13557cc7
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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