4-Nitrobenzenesulfonyl chloride → HCID 20522969, compound

HRID 223239Notes

Reaction equation

HRID 223239 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])[S: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][S:11]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 20522758HCID 20522758, compound

Product 1

HCID 20522969HCID 20522969, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzothiepin-1-yl)methoxy]ethanol and triethylamine is added p-nitrobenzenesulfonyl chloride. The reaction mixture is stirred at room temperature for 30 minutes. The reaction mixture is then 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 to give 2-[(1,3,4,5-tetrahydro-7,8-dimethoxy-2-benzothiepin-1-yl)methoxy]ethyl 4-nitrobenzenesulfonate.

Workup

  1. extractionThe reaction mixture is then extracted with aqueous sodium bicarbonate and brine
  2. filtrationThe organic layer is filtered through sodium sulfate
  3. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-781257b23c9d49aebb5016af5e115aae
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

Loading…