Sodium Chloride → 1-(3-bromopropyl)-3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237514Notes

Reaction equation

HRID 2237514 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[NH:10][S:9]1(=[O:19])=[O:18].[Br:20][CH2:21][CH2:22][CH2:23]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Na+]>O1CCCC1>[Br:20][CH2:21][CH2:22][CH2:23][N:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH2:13][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:19])=[O:18]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 68581770HCID 68581770, compound

Product 1

HCID 685842831-(3-bromopropyl)-3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxideYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.25 g, 0.9 mmol), 3-bromopropanol (0.094 mL, 1.1 mmol), diisopropylazodicarboxylate (0.21 mL, 1.08 mmol), and triphenylphosphine (0.28 g, 1.08 mol) in tetrahydrofuran (3 mL) were stirred at room temperature for 16 hours. The reaction was poured into saturated aqueous sodium chloride (20 mL) and extracted with ethyl acetate. The organics were dried over anhydrous sodium sulfate and concentrated on silica gel (0-100° C. ethyl acetate/hexane) to provide 1-(3-bromopropyl)-3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.17 g, 47%) as a yellow solid:

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried over anhydrous sodium sulfate
  3. concentrationconcentrated on silica gel (0-100° C. ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d04f5144a73e4b459477845a0bd59658
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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