2-Bromoethanol → 1-(2-Bromoethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818793Notes

Reaction equation

HRID 1818793 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]1([N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[NH:23][S:22]2(=[O:31])=[O:30])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Br:32][CH2:33][CH2:34]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:32][CH2:33][CH2:34][N:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:22]1(=[O:30])=[O:31]

Participants

6

Reactant 4

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 468330931-Phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 687112711-(2-Bromoethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.47 mL, 2.4 mmol, 1.2 equiv.) was added dropwise to a solution of 1-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared in an analogous manner as described in general procedure I, 493 mg, 2.00 mmol), 2-bromoethanol (275 mg, 2.20 mmol, 1.1 equiv.) and triphenylphosphine (630 mg, 2.40 mmol, 1.2 equiv.) in dry THF (10 mL) at 0° C. under nitrogen. The solution was stirred overnight while warming to room temperature. Solvent was removed and the oil residue was pre-adsorbed onto Florisil and purified via Isco flash column chromatography (40-g redisep silica gel column, 0-30% ethyl acetate/hexane) to give 706 mg (86%) of 1-(2-bromoethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide as a viscous, colorless liquid. HRMS: calculated for C14H13BrN2O2S+Na+, 374.9773; found (ESI, [M+H]+), 374.9780.

Workup

  1. customprepared in an analogous manner
  2. customat 0° C.
  3. customSolvent was removed
  4. custompurified via Isco flash column chromatography (40-g redisep silica gel column, 0-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-69b02c1aee8c4380b2697bcf2f26ef00
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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