Diisopropylethylamine → Acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl ester

HRID 604459Notes

Reaction equation

HRID 604459 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[N:6][N:5]=1)([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:32][Si:33]([CH3:40])([CH3:39])[CH2:34][CH2:35][O:36][CH2:37]Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]([C:4]1[S:8][C:7]([N:9]([CH2:37][O:36][CH2:35][CH2:34][Si:33]([CH3:40])([CH3:39])[CH3:32])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 57543180Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester

Product 1

HCID 57543195Acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl esterYield 59.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3.3 g Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester were dissolved in 12 ml dichloromethane. 2.69 ml N,N-diisopropylethylamine, 78 mg 4-dimethylaminopyridine and 2.1 g 2-(trimethylsilyl)ethoxymethyl chloride were added. The reaction mixture was stirred at room temperature for one hour. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel with the eluents n-heptane:ethyl acetate=1:1=>1:3 to obtain 2.7 g acetic acid 4-[(5-isopropyl-[1,3,4]thiadiazol-2-yl)-(2-trimethylsilanyl-ethoxymethyl)-sulfamoyl]-phenyl ester.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel with the eluents n-heptane

Sources & evidence

ORD record
ord-89c77b4874e346909e63c8197d0f79e7
Source dataset
uspto-grants-2011_03
Patent number
US07910612B2

Reaction notes

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