Triethylamine → [(Z)-[3-[[2-(4-fluorophenyl)-2-hydroxyethyl]-methylsulfamoyl]-5,6-dihydro-4H-1-benzothiophen-7-ylidene]amino] N-trimethylsilylcarbamate

HRID 1351331Notes

Reaction equation

HRID 1351331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:26])[CH2:9][N:10]([CH3:25])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20]/[C:19](=[N:23]/[OH:24])/[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][Si:35]([N:38]=[C:39]=[O:40])([CH3:37])[CH3:36].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:34][Si:35]([NH:38][C:39]([O:24]/[N:23]=[C:19]1/[CH2:20][CH2:21][CH2:22][C:15]2[C:14]([S:11]([N:10]([CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:26])[CH3:25])(=[O:13])=[O:12])=[CH:18][S:17][C:16]/1=2)=[O:40])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 70696Trimethylsilyl isocyanateHCID 11350049(7e)-7-Hydroxyimino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid[2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide

Product 1

HCID 140032406[(Z)-[3-[[2-(4-fluorophenyl)-2-hydroxyethyl]-methylsulfamoyl]-5,6-dihydro-4H-1-benzothiophen-7-ylidene]amino] N-trimethylsilylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the compound (1.0 g) of Example 1 in toluene (10 mL) was added triethylamine (1.75 mL) and trimethylsilyl isocyanate. After stirring at room temperature for 2 hours, the solution was dilutied with ethyl acetate, and the resulting insoluble matter was extracted, the crude product that were obtained by removing the solvent by evaporation was purified by NH-silica gel column chromatography (ethyl acetate/hexane), and a pale yellow oily substance (1.0 g) was obtained.

Workup

  1. extractionthe resulting insoluble matter was extracted

Sources & evidence

ORD record
ord-b713f7560c904fadb51aeb23c24d0818
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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