Water → HCID 19816549, compound

HRID 2248175Notes

Reaction equation

HRID 2248175 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].O>CSC.CN(C=O)C>[CH3:1][CH:2]([S:5][C:6]1[CH:7]=[CH:8][C:9]([S:12][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 15662554HCID 15662554, compound

Product 1

HCID 19816549HCID 19816549, compound

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionthe aqueous phase is extracted with ether
  2. washThe combined organic layers are washed with 5% sodium hydroxide, with water and with brine
  3. customdried
  4. customthe solvent removed

Sources & evidence

ORD record
ord-42ce7a26c0f5401aaa4acac30a3c203a
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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