Hydrochloric Acid → B-[3-(1,3,4-Thiadiazol-2-ylamino)phenyl]boronic acid

HRID 1894183Notes

Reaction equation

HRID 1894183 reaction equation
[Li+].[OH-:2].[S:3]1[CH:7]=[N:6][N:5]=[C:4]1[NH:8][C:9]1[CH:10]=[C:11]([B-:15](F)(F)F)[CH:12]=[CH:13][CH:14]=1.[K+].[NH4+].[Cl-].Cl.[OH2:23]>CC#N.CCOC(C)=O>[S:3]1[CH:7]=[N:6][N:5]=[C:4]1[NH:8][C:9]1[CH:10]=[C:11]([B:15]([OH:23])[OH:2])[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 131730818HCID 131730818, compound

Product 1

HCID 59277827B-[3-(1,3,4-Thiadiazol-2-ylamino)phenyl]boronic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiOH (340 mg, 14 mmol) was added to a stirred solution of Potassium [3-([1,3,4]Thiadiazol-2-ylamino)-phenyl]trifluoroborate (1.15 g, 4 mmol) in CH3CN (20 ml) and H2O (10 ml) at RT. The reaction was stirred at RT for 20 hours. The mixture was treated with saturated aqueous NH4Cl (32 ml) and 2N HCl (5 ml) to give ˜pH5. EtOAc was added and the precipitate was collected by filtration. The aqueous layer was extracted with CH2Cl2 (×2). The combined extracts were evaporated and the residue was combined with the solid from above. This material was suspended in EtOAc. The solid was collected by filtration and then dried to give the title compound (1.1 g) beige solid. 1H NMR (400 MHz, DMSO-d6) mixture, possibly of the boronic acid and cyclic species. This material was used without further purification.

Workup

  1. customto give ˜pH5
  2. filtrationthe precipitate was collected by filtration
  3. extractionThe aqueous layer was extracted with CH2Cl2 (×2)
  4. customThe combined extracts were evaporated
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-1aa4c9ef6b694958a044b460a34380c6
Source dataset
uspto-grants-2013_08
Patent number
US08513276B2

Reaction notes

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