O-Phenylenediamine → Ethyl 3-{[(3'-{[(2-aminoanilino)carbothioyl]amino}[1,1'-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate

HRID 10946

Reaction equation

HRID 10946 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([NH:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:16])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:31](Cl)(Cl)=[S:32].[C:35]1([NH2:42])[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:41]>C1(C)C=CC=CC=1.O1CCCC1.C1(C)C=CC=CC=1>[NH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:42][C:31]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([NH:17][CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:16])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)=[S:32]

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 10040ThiophosgeneHCID 21982473Ethyl 3-{[(3'-amino[1,1'-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate

Product 1

HCID 21982385Ethyl 3-{[(3'-{[(2-aminoanilino)carbothioyl]amino}[1,1'-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

31.84 g (75 mmol) ethyl 3-{[(3′-amino[1,1′-biphenyl]-3-yl)sulfonyl]amino}-3-phenyl-propanoate 10.1.2 were dissolved in 600 ml toluene and 8.62 g thiophosgene were added. The mixture was refluxed for 2 h, evaporated and the residue dissolved in 200 ml toluene. This solution was added dropwise to a solution of o-phenylendiamine (12.2 g 113 mmol) in 500 ml tetrahydrofurane/toluene (1/1) at 40° C. The mixture was stirred for 12 h at room temperature, concentrated and purified (flash chromatography: dichloromethane/acetic acid ethyl ester 10+1) to yield 43 g (100%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customevaporated
  3. dissolutionthe residue dissolved in 200 ml toluene
  4. concentrationconcentrated
  5. custompurified (flash chromatography: dichloromethane/acetic acid ethyl ester 10+1)
  6. customto yield 43 g (100%)

Sources & evidence

ORD record
ord-796ff312c8e04ffba5526c15fe31e9ab
Source dataset
uspto-grants-2006_08
Patent number
US07094911B2

Linked notes

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