Hydrochloric Acid → HCID 178526658, compound

HRID 2292832Notes

Reaction equation

HRID 2292832 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([Cl:17])[C:9]=1[N:18]=[C:19]=S.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([Cl:17])[C:9]=1[N:18]=[C:19]1[NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1045PutrescineHCID 14798Sodium HydroxideHCID 1263558922133-98-8

Product 1

HCID 178526658HCID 178526658, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.76 g (0.02 mol) of 1,4-diaminobutane in 10 mL of toluene was cooled to -10° C. and 2,6-dichloro-4-nitrophenylisothiocyanate (2.45 g, 0.01 mol) in 10 mL of toluene was added dropwise over 30 minutes. The resulting mixture was stirred an additional hour then heated at reflux overnight. The reaction was cooled to room temperature and was treated with 30 mL 1M HCl. The aqueous phase was brought to pH 9 with 1M NaOH and the resulting yellow precipitate was filtered, washed with water then hexane and air dried to give 0.92 g (30%) of the product.

Workup

  1. temperaturethen heated
  2. temperatureat reflux overnight
  3. filtrationthe resulting yellow precipitate was filtered
  4. washwashed with water
  5. dry with materialhexane and air dried

Sources & evidence

ORD record
ord-627aab5f1a7d4553b844cee3708b0a79
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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