Thionyl Chloride → HCID 23448964, compound

HRID 2185458Notes

Reaction equation

HRID 2185458 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][S:15]([O-])(=[O:17])=[O:16])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].S(Cl)([Cl:24])=O>>[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][S:15]([Cl:24])(=[O:17])=[O:16])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22458570HCID 22458570, compound

Product 1

HCID 23448964HCID 23448964, compound

Procedure

Thionyl chloride (20 mL) was added to sodium 2-(4-nitrobenzyloxycarbonylamino)-ethanesulfonate (A, 1.25 g). After stirring at room temperature for 10 min, the mixture was refluxed for 3 hr and concentrated in vacuo. The residue was suspended in benzene and the mixture was filtered over diatomaceous earth. The filtrate was concentrated in vacuo to afford the title compound (0.1 g) as a white powder: 1H NMR (400 MHz, CDCl3) δ 3.82-3.97 (m, 4H), 5.23 (s, 2H), 5.43 (br s, 1H), 7.51 (d, J=8.8 Hz, 2H), and 8.23 (d, J=8.8 Hz, 2H).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. concentrationconcentrated in vacuo
  3. filtrationthe mixture was filtered over diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d6d85726cdd1410b9c675c7964f26073
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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