Diisopropylethylamine → HCID 67044168, compound

HRID 1944476Notes

Reaction equation

HRID 1944476 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[S:10](=[O:19])(=[O:18])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C.[CH3:30][Si:31]([CH3:38])([CH3:37])[CH2:32][CH2:33][O:34][CH2:35]Cl>ClCCl>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[S:10](=[O:19])(=[O:18])[N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:38])([CH3:37])[CH3:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether2×HCID 67044506HCID 67044506, compound

Product 1

HCID 67044168HCID 67044168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenylsulfamoylnicotinic acid methyl ester (1.1 g), N,N-diisopropylethylamine (1.9 mL) and dichloromethane at 0° C. was treated with 2-(trimethylsilyl)ethoxymethyl chloride (0.67 mL), and the resulting mixture was stirred at room temperature overnight. The mixture was cooled to 0° C., treated with additional (trimethylsilyl)ethoxymethyl chloride (0.30 mL), and stirred at room temperature for 5 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (0:1 to 1:0 by volume) to afford the title compound (1.6 g).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirred at room temperature for 5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and cyclohexane (0:1 to 1:0 by volume)

Sources & evidence

ORD record
ord-cc5bbaebfaeb480b8697752dd40bc9ac
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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