2-Bromoethanol → HCID 68711995, compound

HRID 1818813Notes

Reaction equation

HRID 1818813 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][C:15]=2[F:21])[S:6]1(=[O:23])=[O:22].[Br:24][CH2:25][CH2:26]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>O1CCCC1>[Br:24][CH2:25][CH2:26][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][C:15]=2[F:21])[S:6]1(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68714257HCID 68714257, compound

Product 1

HCID 68711995HCID 68711995, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1-(3-bromopropyl)-3-(4-chloro-2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (150 mg, 0.502 mmol), 2-bromoethanol (71 uL, 1.00 mmol), and triphenylphosphine (263 mg, 1.00 mmol) in anhydrous tetrahydrofuran was added diisopropylazodicarboxylate (195 uL, 1.00 mmol) and the solution stirred, capped, at room temperature for 18 hr. The reaction mixture was concentrated then loaded directly onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-25% ethyl acetate in hexane to afford 0.07 g of 1-(2-bromoethyl)-3-(4-chloro-2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide as a white solid.

Workup

  1. customcapped, at room temperature for 18 hr
  2. concentrationThe reaction mixture was concentrated
  3. custompurified via Isco chromatography (Redisep, silica, gradient 0-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4f228473f8b5483da914552173793d31
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

Loading…