Benzenesulfonyl chloride → HCID 178477576, compound

HRID 853122Notes

Reaction equation

HRID 853122 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1)([O:8][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])[C:4]([F:7])([F:6])[F:5].CCN(C(C)C)C(C)C.[C:34]1([S:40](Cl)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[C:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH:22][S:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:42])=[O:41])[CH2:18][CH2:17]1)([O:8][Si:9]([CH2:10][CH3:11])([CH2:14][CH3:15])[CH2:12][CH3:13])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178477569HCID 178477569, compound

Product 1

HCID 178477576HCID 178477576, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.71 g (1.87 mmol) of trans 4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexylamine in 5 mL of CH2Cl2 was treated with 0.64 mL (3.74 mmol) of DIPEA and 0.24 mL (1.87 mmol) of benzenesulfonylchloride and stirred at RT for 3 hrs. Distribution of the crude mixture between a diluted aqueous solution of HCl and Et2O, drying of the combined organic phases over Na2SO4 and chromatography on silica gel with EtOAc/heptane 1:1 gave 0.9 g (93%) of trans-N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzenesulfonamide as a light yellow semisolid, MS: 518 (M−H).

Workup

  1. dry with materialDistribution of the crude mixture between a diluted aqueous solution of HCl and Et2O, drying of the combined organic phases over Na2SO4 and chromatography on silica gel with EtOAc/heptane 1:1

Sources & evidence

ORD record
ord-1d5233e58c124aff91d41afb6a9244e1
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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