Sodium Carbonate → N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine

HRID 502562Notes

Reaction equation

HRID 502562 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=2[CH:15]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:16]1([C:2]2[CH:3]=[CH:4][C:5]3[S:9][N:8]=[C:7]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[C:6]=3[CH:15]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58726901N1-(5-bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine

Product 1

HCID 58727100N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N1-(5-bromobenzo[d]isothiazol-3-yl)propane-1,3-diamine (100 mg, 0.35 mmol), phenylboronic acid (43 mg, 0.35 mmol), tetrabutylammonium bromide (115 mg, 0.35 mmol), sodium carbonate (110 mg, 1.05 mmol) and palladium (II) acetate (1 mg) in water (3 mL) was microwaved at 150° C. for 5 min. The reaction was diluted with methylene chloride and the mixture was washed successively with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting product, N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine, was carried forward without further purification. MW=238 confirmed by LC-MS, tr=2.73 min (Method B) MH+=237-239

Workup

  1. customwas microwaved at 150° C. for 5 min
  2. washthe mixture was washed successively with aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting product, N1-(5-Phenylbenzo[d]isothiazol-3-yl)propane-1,3-diamine, was carried forward without further purification
  7. customconfirmed by LC-MS, tr=2.73 min (Method B) MH+=237-239

Sources & evidence

ORD record
ord-07fa30e7e9be4e9c974381d6be3e0cf9
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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