Dimethylformamide → 2-Nitro-5-[(3-phenylpropyl)sulfanyl]aniline

HRID 1730819Notes

Reaction equation

HRID 1730819 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].O.[S-2:13].[Na+].[Na+].CN(C)C=O.[C:21]1([CH2:27][CH2:28][CH2:29]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[NH2:1][C:2]1[CH:7]=[C:6]([S:13][CH2:29][CH2:28][CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 12503(3-Bromopropyl)benzeneHCID 742185-Chloro-2-nitroanilineHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 214965152-Nitro-5-[(3-phenylpropyl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.45 G. of 2-amino-4-chloro-1-nitrobenzene and 5.3 g. of sodium sulfide monohydrate in 30 ml. of dimethylformamide is heated at about 100° for 1 hour under nitrogen, cooled and 4.5 g. of 3-phenylpropyl bromide added, held at 20°-25° for 4 hours, then diluted with water. The product is filtered off and recrystallized from methanol to afford 2-amino-4-(3-phenylpropylthio)-1-nitrobenzene.

Workup

  1. temperaturecooled
  2. filtrationThe product is filtered off
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7e18a164a36d48a6b6c3310db1e5ef48
Source dataset
uspto-grants-1976_11
Patent number
US03993768

Reaction notes

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