Taurine → HCID 22458570, compound

HRID 2185457Notes

Reaction equation

HRID 2185457 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].C(=O)([O-])[O-].[Na+:12].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16].C(OCC)C>C(OCC)C.O>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:15]([NH:1][CH2:2][CH2:3][S:4]([O-:7])(=[O:6])=[O:5])=[O:16])=[CH:24][CH:23]=1)([O-:27])=[O:26].[Na+:12]

Participants

6

Reactant 4

HCID 1123TaurineHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 22458570HCID 22458570, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-aminoethanesulfonic acid (5.0 g) and sodium carbonate (9.4 g) in ethyl ether-water (100 mL, 1:1, v/v), at 0° C., was treated with 4-nitrobenzyl chloroformate (8.6 g). After stirring vigorously at 0° C. for 10 min and at room temperature for 15 hr, ethyl ether was added to the reaction mixture. The precipitates were collected by filtration and washed with ethyl ether to afford the title compound (9.2 g) as a white powder: 1H NMR (400 MHz, D2O) δ 2.94 (t, J=6.4 Hz, 2H), 3.39 (t, J=6.4 Hz, 2H), 5.09 (s, 2H), 7.44 (d, J=8.3 Hz, 2H), and 8.11 (d, J=8.3 Hz, 2H).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with ethyl ether

Sources & evidence

ORD record
ord-440df451cf9b4ef9b23cfc295d1f21bf
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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