Water → HCID 11563823, compound

HRID 899563Notes

Reaction equation

HRID 899563 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[C:16]1[C:17](CCCC2C=CC=CC=2)=[C:18](S([O-])(=O)=O)C=CC=1C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]([NH:39][CH2:40][CH2:41][CH:42]([C:49]1[CH:54]=[C:53]([CH3:55])[CH:52]=[CH:51][C:50]=1[O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH3:38])[CH3:37].O>CS(C)=O>[CH2:57]([O:56][C:50]1[CH:51]=[CH:52][C:53]([CH3:55])=[CH:54][C:49]=1[CH:42]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:41][CH2:40][N:39]([CH2:18][CH2:17][CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:36]([CH3:38])[CH3:37])[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11696440HCID 11696440, compoundHCID 86604788HCID 86604788, compound

Product 1

HCID 11563823HCID 11563823, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(2-(benzyloxy)-5-methylphenyl)-3-phenylpropyl-4-methylbenzenesulfonate of Formula IVa (120 g) and N-isopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropylamine (92 g) in dimethylsulfoxide (600 ml) was heated at 60-70° C. for 18-20 hours. The reaction mass was cooled to 25-35° C., decomposed with water (600 ml), and extracted with toluene (600 ml). The toluene layer was washed with a mixture of concentrated hydrochloric acid (60 ml) and water (606 ml). The organic layer was then washed with 10% sodium hydroxide solution (240 ml), followed by water (600 ml). The organic layer was distilled completely to obtain the title compound as a syrup. Yield: 128 g (75.4%).

Workup

  1. temperatureThe reaction mass was cooled to 25-35° C.
  2. extractionextracted with toluene (600 ml)
  3. washThe toluene layer was washed with a mixture of concentrated hydrochloric acid (60 ml) and water (606 ml)
  4. washThe organic layer was then washed with 10% sodium hydroxide solution (240 ml)
  5. distillationThe organic layer was distilled completely

Sources & evidence

ORD record
ord-a12cfb97cc16412e912c0df4ba59bf84
Source dataset
uspto-grants-2008_04
Patent number
US07355077B2

Reaction notes

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