Hydrazine hydrate (1:1) → HCID 15662556, compound
Reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:8][CH:7]=1)[CH2:3][CH3:4].O.NN>>[CH3:1][CH:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=1)[CH2:3][CH3:4]Participants
3
Procedure
To 4-(1-methylpropylthio)benzenethiol (8.79 g, 44.3 mmol) in 25 ml of DMS is added, under N2, potassium carbonate (7.05 g, 51.0 mmol) followed by dropwise addition of N-(bromoethyl)-phthalimide (12.94 g, 51.0 mmol) in 30 ml of DMF. The mixture is stirred at RT overnight. Water is then added and the aqueous phase is extracted with ether. The combined organic layers are washed with 5% sodium hydroxide, with water and with brine, dried and the solvent removed to give N-{2-[4-(1-methylpropylthio)-phenylthio]ethyl}phthalimide. Following the procedures of Example 13, the above phthalimide (2.12 g, 5.7 mmol is reacted with hydrazine hydrate (0.28 ml, 5.7 mmol) to give 2-[4-(1-methylpropylthio)phenylthio ethylamine.
Sources & evidence
- ORD record
- ord-7d6257cad36f4b6eb886468e9bae1408
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037991
Reaction notes
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