Water → HCID 19759104, compound

HRID 1646996Notes

Reaction equation

HRID 1646996 reaction equation
[CH:1]([C:4]1[O:5][CH:6]=[CH:7][C:8]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21]Br)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:3])[CH3:2].[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24].O.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>CS(C)=O>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH:1]([C:4]1[O:5][CH:6]=[CH:7][C:8]=1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][NH:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 6385Tert-ButylamineHCID 10385520HCID 10385520, compound

Product 1

HCID 19759104HCID 19759104, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.00282 mol of 2-isopropyl-3-[4-(3-bromopropyloxy)benzenesulphonyl]furan and 0.013 mol of tert-butylamine in 7 ml of dimethylsulphoxide was stirred at room-temperature for 24 hours. After that, the mixture was poured into water, distilled in the presence of ethyl acetate, dried on sodium sulphate, filtered and concentrated. The residue so obtained was purified on a silica column using a methanol/ethyl acetate 2/8 mixture as eluent. The oily base so provided was then treated with an ethereal solution of oxalic acid and the precipitate was recrystallized from ethanol.

Workup

  1. distillationdistilled in the presence of ethyl acetate
  2. customdried on sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue so obtained
  6. customwas purified on a silica column
  7. customThe oily base so provided
  8. customthe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-502ce601b6414cd2b54709648a3be680
Source dataset
uspto-grants-1993_01
Patent number
US05182291

Reaction notes

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