Ethanol → Tris(2,4-bis(N,N-bis(2-hydroxyethyl)sulfamoyl)phenyl)bismuthine

HRID 2839

Reaction equation

HRID 2839 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:154][CH2:155][O:156][Si](C(C)(C)C)(C)C)[S:12]([C:15]1[CH:20]=[C:19]([S:21](=[O:44])(=[O:43])[N:22]([CH2:33][CH2:34][O:35][Si](C(C)(C)C)(C)C)[CH2:23][CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH:18]=[CH:17][C:16]=1[Bi:45]([C:100]1[CH:105]=[CH:104][C:103]([S:106](=[O:129])(=[O:128])[N:107]([CH2:118][CH2:119][O:120][Si](C(C)(C)C)(C)C)[CH2:108][CH2:109][O:110][Si](C(C)(C)C)(C)C)=[CH:102][C:101]=1[S:130](=[O:153])(=[O:152])[N:131]([CH2:142][CH2:143][O:144][Si](C(C)(C)C)(C)C)[CH2:132][CH2:133][O:134][Si](C(C)(C)C)(C)C)[C:46]1[CH:51]=[CH:50][C:49]([S:52](=[O:75])(=[O:74])[N:53]([CH2:64][CH2:65][O:66][Si](C(C)(C)C)(C)C)[CH2:54][CH2:55][O:56][Si](C(C)(C)C)(C)C)=[CH:48][C:47]=1[S:76](=[O:99])(=[O:98])[N:77]([CH2:88][CH2:89][O:90][Si](C(C)(C)C)(C)C)[CH2:78][CH2:79][O:80][Si](C(C)(C)C)(C)C)(=[O:14])=[O:13])(C(C)(C)C)(C)C.C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[OH:80][CH2:79][CH2:78][N:77]([CH2:88][CH2:89][OH:90])[S:76]([C:47]1[CH:48]=[C:49]([S:52](=[O:75])(=[O:74])[N:53]([CH2:64][CH2:65][OH:66])[CH2:54][CH2:55][OH:56])[CH:50]=[CH:51][C:46]=1[Bi:45]([C:100]1[CH:105]=[CH:104][C:103]([S:106](=[O:129])(=[O:128])[N:107]([CH2:118][CH2:119][OH:120])[CH2:108][CH2:109][OH:110])=[CH:102][C:101]=1[S:130](=[O:153])(=[O:152])[N:131]([CH2:142][CH2:143][OH:144])[CH2:132][CH2:133][OH:134])[C:16]1[CH:17]=[CH:18][C:19]([S:21](=[O:43])(=[O:44])[N:22]([CH2:33][CH2:34][OH:35])[CH2:23][CH2:24][OH:25])=[CH:20][C:15]=1[S:12](=[O:13])(=[O:14])[N:11]([CH2:10][CH2:9][OH:8])[CH2:154][CH2:155][OH:156])(=[O:98])=[O:99]

Participants

5

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 10606600tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine

Product 1

HCID 10844129Tris(2,4-bis(N,N-bis(2-hydroxyethyl)sulfamoyl)phenyl)bismuthineYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

13.59 g of the tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine preparation prepared in Example 5 was dissolved in a mixed solvent containing 13.6 ml of ethanol and 27 ml of dichloromethane, and 0.272 g of p-toluenesulfonic acid monohydrate was added thereto. The mixture was refluxed under heating at 50° C. for 6 hours, and then cooled to room temperature. The crystals were collected by filtration, washed with 29.5 ml of dichloromethane and dried. As a result, 5.54 g of the title compound was obtained as crystals with a melting point of 110°-113° C.

Workup

  1. customprepared in Example 5
  2. dissolutionwas dissolved in a mixed solvent
  3. additionwas added
  4. temperatureThe mixture was refluxed
  5. temperaturecooled to room temperature
  6. filtrationThe crystals were collected by filtration
  7. washwashed with 29.5 ml of dichloromethane
  8. customdried

Sources & evidence

ORD record
ord-39d007a1ceb040768775ffb5002a1d9e
Source dataset
uspto-grants-1998_03
Patent number
US05730953

Linked notes

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