1,2-Dichloroethane → HCID 24744053, compound

HRID 1642059Notes

Reaction equation

HRID 1642059 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=O)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(Cl)CCl.CCN(C(C)C)C(C)C.[NH2:38][C:39]1[CH:40]=[C:41]([N:45]2[S:49](=[O:51])(=[O:50])[NH:48][C:47](=[O:52])[CH2:46]2)[CH:42]=[CH:43][CH:44]=1.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.C1(C)C=CC=CC=1.CCOC(C)=O.C1(C)C=CC=CC=1>[O:51]=[S:49]1(=[O:50])[NH:48][C:47](=[O:52])[CH2:46][N:45]1[C:41]1[CH:40]=[C:39]([NH:38][C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:15][CH:14]=3)=[CH:21][CH:20]=2)=[O:24])[CH:44]=[CH:43][CH:42]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acidHCID 66755815HCID 66755815, compound

Product 1

HCID 24744053HCID 24744053, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

1.06 mmol of 4′-(octyloxy)-4-biphenyl-carboxylic acid, 1.06 mmol of EDC and 1.06 mmol DIPEA are added to a mixture of 0.53 mmol of 5-(3-amino-phenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one and 0.11 mmol of HOAt in 6 ml of a DMF/toluene-mixture. The mixture obtained is stirred at rt for 18 hours, diluted with EtOAc and toluene and a precipitate is obtained and filtered off. 4′-Octyloxy-biphenyl-4-carboxylic acid [3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)phenyl]-amide in solid form is obtained. The filtrate obtained is washed with HCl (1M) and brine, the organic layer is dried and solvent is evaporated. Further 4′-octyloxy-biphenyl-4-carboxylic acid [3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-amide is obtained.

Workup

  1. customThe mixture obtained
  2. customa precipitate is obtained
  3. filtrationfiltered off

Sources & evidence

ORD record
ord-0b7cf361b4f045e1acc5e73accea5a85
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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