Bicarbonate Ion → HCID 19907906, compound

HRID 1534754Notes

Reaction equation

HRID 1534754 reaction equation
Cl[S:2]([C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])=[O:3].[NH2:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].C(=O)(O)[O-].[Na+].C(=O)(O)[O-]>ClCCl.O>[CH3:21][Si:20]([CH3:22])([NH:19][S:2]([C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])=[O:3])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 516892Sodium BicarbonateHCID 124271471-tert-Butyl-1,1-dimethylsilanamineHCID 19907909HCID 19907909, compound

Product 1

HCID 19907906HCID 19907906, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl 2-(chlorosulfonyl)-3-nitrobenzoate (14.7 g), amino-t-butyldimethylsilane (15.4 g), and sodium bicarbonate (3.5 g) in dichloromethane (300 mL) was stirred at room temperature in a stoppered flask for 4 days. Water (90 mL) and saturated aqueous bicarbonate (45 mL) were added, and the mixture was stirred. The dichloromethane phase was dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel eluted with 20% ethyl acetate in hexanes to give 12.9 g of the title compound as a white solid, m.p. 101-102° C.

Workup

  1. stirringthe mixture was stirred
  2. dry with materialThe dichloromethane phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. washeluted with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d988b4de0dde46d5ba9741f8224bd56d
Source dataset
uspto-grants-1992_02
Patent number
US05090993

Reaction notes

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