Propyl mercaptan → HCID 66937156, compound

HRID 538166Notes

Reaction equation

HRID 538166 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([SH:22])[CH2:20][CH3:21]>CN(C=O)C>[Cl:1][C:2]1[C:7]([S:22][CH2:19][CH2:20][CH3:21])=[CH:6][C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroaniline

Product 1

HCID 66937156HCID 66937156, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4,5-dichloro-2-nitro-phenylamine (3.50 g, 16.9 mmol), potassium carbonate (4.67 g, 33.8 mmol), and DMF (85 mL) was added 1-propanethiol (2.30 mL, 25.4 mmol). The reaction mixture was heated at 90° C. for 1.5 h, and allowed to cool to 23° C. The mixture was poured into ice/brine (600 mL) and the resulting precipitate was collected to yield the titled compound (4.09 g, 98%). 1H NMR (600 MHz, CDCl3): 8.11 (s, 1H), 6.46 (s, 1H), 6.10 (br s, 2H), 2.91 (t, J=7.3 Hz, 2H), 1.85-1.76 (m, 2H), 1.12 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureto cool to 23° C
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-36064922de0f44bd9b34e61dfe142071
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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