Hydrochloric Acid → HCID 178526659, compound

HRID 2292831Notes

Reaction equation

HRID 2292831 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Cl:16])[C:8]=1[N:17]=[C:18]=S.Cl>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Cl:16])[C:8]=1[N:17]=[C:18]1[NH:5][CH2:4][CH2:3][CH2:2][NH:1]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4281,3-PropanediamineHCID 1263558922133-98-8

Product 1

HCID 178526659HCID 178526659, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.65 mL (0.02 mol) of 1,3-diaminopropane in toluene (10 mL) was cooled to -10° C. using an ice/methanol bath. To this solution was added 2,6-dichloro-4-nitrophenylisothiocyanate (2.45 g, 0.01 mol) in toluene (10 mL) dropwise over 30 minutes, which reacted to form a red oil. The reaction was stirred for an additional 2 hours, then heated at reflux for 4 hours. The mixture was cooled to room temperature then treated with 30 mL of 1 M HCl. After filtration of some insoluble material, the biphasic mixture was separated and the aqueous phase was basified to pH 9 using 1M NaOH. The resulting yellow precipitate was collected by filtration, washed with water, then hexane and air dried to give 0.6 g (21%) of the product.

Workup

  1. customwhich reacted
  2. customto form a red oil
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. filtrationAfter filtration of some insoluble material
  6. customthe biphasic mixture was separated
  7. filtrationThe resulting yellow precipitate was collected by filtration
  8. washwashed with water
  9. dry with materialhexane and air dried

Sources & evidence

ORD record
ord-a5da8d72ce0d4d2795949b7b8e5b786a
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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