Benzoyl isothiocyanate → HCID 59337717, compound

HRID 12399Notes

Reaction equation

HRID 12399 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[NH2:22])[CH2:12]2)[CH2:8][CH2:7]1)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:27]([N:35]=[C:36]=[S:37])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:1]([N:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[NH:22][C:36]([NH:35][C:27](=[O:34])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[S:37])[CH2:12]2)[CH2:8][CH2:7]1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 59337728HCID 59337728, compound

Product 1

HCID 59337717HCID 59337717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 20f (118 mg, 0.33 mmol) and benzoylisothiocyanate (63 μL, 0.47 mmol) in DCM (3 mL) was stirred at rt for 3 h. The reaction was concentrated and the residue was purified by flash chromatography (silica gel, 0-10% MeOH/DCM) to give 20 g, as yellow solid (156 mg). LC-MS m/z 513.06 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography (silica gel, 0-10% MeOH/DCM)
  3. customto give 20 g

Sources & evidence

ORD record
ord-9c1f04891eae4e6f995f2661eafdbac1
Source dataset
uspto-grants-2010_06
Patent number
US07728008B2

Reaction notes

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