2-Aminothiophenol → NSC506645

HRID 898074Notes

Reaction equation

HRID 898074 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7](/[CH:8]=[CH:9]/[CH2:10]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[SH:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:7](/[CH:8]=[CH:9]/[C:10]2[S:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 10340Sodium CarbonateHCID 22673539HCID 22673539, compound

Product 1

HCID 6143420NSC506645Yield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

trans-4-Nitrocinnamyl chloride 10 (1.77 g, 9.5 mmol, 1.2 eq.) in DMF (20 ml) was added dropwise to a solution of 2-aminothiophenol 9 (1.0 g, 8.0 mmol) in DMF(15 ml) at room temperature. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was poured into a solution of 10% sodium carbonate (100 ml). The participate was collected by filtration under reduced pressure. Recrystallization from methanol gave 1.92 g (85.1%) of the product 11.

Workup

  1. filtrationThe participate was collected by filtration under reduced pressure
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-24a34c2f2b9348b9894262d50538ecf8
Source dataset
uspto-grants-2008_04
Patent number
US07351401B2

Reaction notes

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