Hydrogen Peroxide → HCID 59828902, compound

HRID 1191068Notes

Reaction equation

HRID 1191068 reaction equation
OO.[NH2:3][C:4]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1)=[CH:5][C:6](=[S:12])[NH:7][CH2:8][CH:9]1[CH2:11][CH2:10]1>CO>[CH:9]1([CH2:8][NH:7][C:6]2[S:12][N:3]=[C:4]([C:13]3[CH:14]=[CH:15][C:16]([CH2:17][NH2:18])=[CH:19][CH:20]=3)[CH:5]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 72572534HCID 72572534, compound

Product 1

HCID 59828902HCID 59828902, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 30% hydrogen peroxide solution (0.13 mL, 1.1 mmol) to a solution of 4-[1-amino-2-(cyclopropylmethyl-thiocarbamoyl)-vinyl]-benzylamine (150 mg, 0.57 mmol) in methanol (5 mL). Stir the solution for 16 h at room temperature. Quench the reaction with aqueous saturated sodium hydrogensulfite (1 mL). Extract the mixture with EtOAc (2×30 mL), collect the organic layer and concentrate in vacuo. Purify the residue by chromatography on silica gel (4 g) eluting with DCM/ammonia in methanol (97:3) to obtain the title compound as a yellow solid (68 mg, 46%). MS (ES+) m/z: 243.1 (M-NH3+H)+.

Workup

  1. customQuench
  2. customthe reaction with aqueous saturated sodium hydrogensulfite (1 mL)
  3. extractionExtract the mixture with EtOAc (2×30 mL)
  4. customcollect the organic layer
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by chromatography on silica gel (4 g)
  7. washeluting with DCM/ammonia in methanol (97:3)

Sources & evidence

ORD record
ord-5ac8197115404fd398bef085e39bbd8e
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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