Sodium Carbonate → HCID 22313945, compound

HRID 270456Notes

Reaction equation

HRID 270456 reaction equation
[CH2:1]([N:3]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:30]=[CH:29][C:15]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:17][S:18][C:14]=2[CH:13]=1)[CH2:4][CH2:5]O)[CH3:2].CCN(S(F)(F)[F:37])CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH2:5][F:37])[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:30]=[CH:29][C:15]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[N:17][S:18][C:14]=2[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 10181629HCID 10181629, compound

Product 1

HCID 22313945HCID 22313945, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 540 mg (11.37 mmol) 2-(Ethyl-{4-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yloxy]-butyl}-amino)-ethanol in 6 ml CH2Cl2 were added 0.22 ml (1.7 mmol) DAST at −78° C. After stirring at that temperature for 3.5 h, additional 0.2 ml (1.6 mmol) DAST were added and the mixture was slowly warmed to RT over night. The solution was added to a cooled aqueous solution of Na2CO3 and extracted with EtOAc. The organic phase was washed with brine and dried over Na2SO4. Column chromatography CH2Cl2:MeOH 95:5 yielded 79.3 mg (16%) Ethyl-(2-fluoro-ethyl)-{4-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yloxy]-butyl}-amine as brown oil, MS: 441 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-092caf71b9eb43d78d7ee4ead0bc4ef8
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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