Water → HCID 19759104, compound

HRID 1032379Notes

Reaction equation

HRID 1032379 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-8223e8e8f4d34139872be2764cf69315
Source dataset
uspto-grants-1990_09
Patent number
US04957925

Reaction notes

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