4-Toluenesulfonyl chloride → HCID 86761441, compound

HRID 561726Notes

Reaction equation

HRID 561726 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:45])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:28]2[CH:33]=[CH:32][C:31]([O:34][Si](C(C)C)(C(C)C)C(C)C)=[CH:30][CH:29]=2)=[C:19](\[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)/[CH2:20][CH3:21])=[CH:14][CH:13]=1.C(N(CC)CC)C.C1(C)C=CC([S:59](Cl)(=O)=O)=CC=1.[F:64][C:65]([F:75])([C:71]([F:74])([F:73])[F:72])[CH2:66][CH2:67][CH2:68]CS>ClCCl>[OH:34][C:31]1[CH:30]=[CH:29][C:28](/[C:18](/[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:9]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:59][CH2:68][CH2:67][CH2:66][C:65]([F:75])([F:64])[C:71]([F:74])([F:73])[F:72])=[O:45])=[CH:17][CH:16]=2)=[C:19](/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)\[CH2:20][CH3:21])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67001278HCID 67001278, compoundHCID 86761442HCID 86761442, compound

Product 1

HCID 86761441HCID 86761441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-N-(6-hydroxyhexyl)-2-(4-(2-phenyl-1-(4-(triisopropylsilyloxy)phenyl)but-1-enyl)phenoxy)acetamide from reaction 3 is dissolved in dichloromethane. To this solution are added triethyl amine and p-toluenesulfonyl chloride in that order. The solution is stirred until the reaction is complete (TLC). 5,5,6,6,6-pentafluorohexanethiol is then added and the mixture stirred until the reaction is complete (TLC). When the reaction is complete, the mixture is washed with dilute hydrochloric acid, dilute sodium bicarbonate and water. The organic layer is the dried over sodium sulfate or other suitable desiccant. The dried suspension is then filtered and concentrated under reduced pressure to afford (Z)-2-(4-(1-(4-hydroxyphenyl)-2-phenylbut-1-enyl)phenoxy)-N-(6-(4,4,5,5,5-pentafluoropentylthio)hexyl)acetamide among other products.

Workup

  1. stirringthe mixture stirred until the reaction
  2. washthe mixture is washed with dilute hydrochloric acid, dilute sodium bicarbonate and water
  3. dry with materialdried over sodium sulfate or other suitable desiccant
  4. filtrationThe dried suspension is then filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b67d4b9f8d440548a72d2f4bc580c81
Source dataset
uspto-grants-2011_11
Patent number
US08063249B1

Reaction notes

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