1-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]propan-2-one → HCID 58858057, compound

HRID 19520Notes

Reaction equation

HRID 19520 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9](=[O:11])[CH3:10])=[N:4][N:3]=1.[BH4-].[Na+]>CO.O.O.CC(O)=O>[NH2:1][C:2]1[S:6][C:5]([S:7][CH2:8][CH:9]([OH:11])[CH3:10])=[N:4][N:3]=1

Participants

6

Reactant 2

HCID 12516891-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]propan-2-oneHCID 4311764Sodium borohydride

Product 1

HCID 58858057HCID 58858057, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of 1-(5-amino-1,3,4-thiadiazol-2-ylthio)propan-2-one (700 mg, 3.7 mmol) in 8 mL of 1:1 MeOH/H2O at rt was added a solution of NaBH4 (159 mg, 4.2 mmol) in 1.5 mL of H2O dropwise over 10 min. The suspension was stirred at rt for 1 h and diluted with 0.6 mL of HOAc followed by 6 mL of H2O. The precipitate was filtered, washed with H2O and dried under vacuum to afford 0.608 g of the title compound (86%) as an off-white solid. 1H NMR (400 MHz, MeOH-d3) δ 1.25 (d, J=6.6 Hz, 3H), 3.06-3.21 (m, 2H), 3.90-4.04 (m, 1H). HPLC (Method #1) 0.710 min retention time, (90%). MS (ES): m/z 192 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-974b7da8cfee40b098125a667db6fa23
Source dataset
uspto-grants-2010_06
Patent number
US07745447B2

Reaction notes

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