Hydrazine hydrate (1:1) → 1-[2-(Tritylsulfanyl)phenyl]methanamine

HRID 2096246Notes

Reaction equation

HRID 2096246 reaction equation
[C:1]([S:20][C:21]1[CH:38]=[CH:37][CH:36]=[CH:35][C:22]=1[CH2:23][N:24]1C(=O)C2C(=CC=CC=2)C1=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[C:1]([S:20][C:21]1[CH:38]=[CH:37][CH:36]=[CH:35][C:22]=1[CH2:23][NH2:24])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 668222702-[2-(Tritylsulfanyl)benzyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 668224941-[2-(Tritylsulfanyl)phenyl]methanamineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[2-(Tritylsulfanyl)benzyl]-1H-isoindole-1,3(2H)-dione (4.7 g, 9.19 mmol) was suspended in EtOH (150 mL) and treated with hydrazine monohydrate 65% (4.66 mL, 62 mmol). The mixture was heated under reflux for 1.5 h, cooled to RT and the precipitate was filtered. The filtrate was concentrated, triturated with EtOAc and filtered. The filtrate was concentrated under reduced pressure to afford the title compound (3.0 g, 86%) as a colourless oil. 1H NMR (300 MHz, CDCl3): δ 7.34-7.28 (6H, m), 7.26-7.18 (9H, m), 7.15 (2H, m), 7.10 (1H, m), 6.93-6.85 (1H, m), 3.40 (2H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. filtrationthe precipitate was filtered
  4. concentrationThe filtrate was concentrated
  5. customtriturated with EtOAc
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eddaee4e719242fea4049542e7578cf4
Source dataset
uspto-grants-2013_05
Patent number
US08450314B2

Reaction notes

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