Triphenylphosphine → HCID 69059545, compound

HRID 1819664Notes

Reaction equation

HRID 1819664 reaction equation
BrCCC[N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[S:6]1(=[O:22])=[O:21].[Cl:23][CH2:24][CH2:25][C@@H:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([N:7]2[S:6](=[O:21])(=[O:22])[N:5]([CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:25][CH2:24][Cl:23])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=3)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 68895397HCID 68895397, compound

Product 1

HCID 69059545HCID 69059545, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-bromopropyl)-3-(4-chlorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.28 g, 1.0 mmol), (S)-(−)-3-chloro-1-phenyl-1-propanol (0.17 g, 1.0 mmol), and triphenylphosphine (314 mg, 1.2 mmol) in anhydrous THF (15 mL) was added DIAD (0.23 mL, 1.2 mmol) under nitrogen at 25° C. The mixture was stirred for 16 hours followed by concentration of the mixture in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 5-40% ethyl acetate in hexane) to afford 0.17 g of 1-(4-Chloro-phenyl)-3-(3-chloro-1-phenyl-propyl)-1,3-dihydro-benzo[1,2,5]-thiadiazole 2,2-dioxide that was immediately carried on to the next step. MS (ESI) m/z [M−H]− 431;

Workup

  1. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 5-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-59534391360648e38a6426d02f8f6d7f
Source dataset
uspto-grants-2009_10
Patent number
US07601744B2

Reaction notes

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