Diisopropylethylamine → HCID 178509206, compound

HRID 425303Notes

Reaction equation

HRID 425303 reaction equation
[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([N:14]=[C:15]=[S:16])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl.[NH2:18][NH:19][C:20](N)=[NH:21].C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH2:21][C:20]1[N:14]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:5][CH:6]=2)[C:15]([SH:16])=[N:18][N:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneHCID 178418668HCID 178418668, compound

Product 1

HCID 178509206HCID 178509206, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Compound 3 (447 mg, 2.1 mmol) was dissolved in 3 mL of dimethylformamide, aminoguanidine hydrochloride salt (355 mg, 3.2 mmol) and diisopropyl ethylamine (0.56 mL, 3.2 mmol) were added and the mixture stirred at 50° C. for 18 hours. The mixture was then concentrated and to the resulting residue was added 2M aqueous sodium hydroxide solution (10 mL). The mixture was stirred at 50° C. for 18 hours and then cooled to room temperature. The resulting mixture was then neutralized with aqueous 1N HCl and the precipitate (product) collected to give 5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (4). (240 mg, 44% yield)

Workup

  1. concentrationThe mixture was then concentrated and to the resulting residue
  2. additionwas added 2M aqueous sodium hydroxide solution (10 mL)
  3. stirringThe mixture was stirred at 50° C. for 18 hours
  4. temperaturecooled to room temperature
  5. customthe precipitate (product) collected

Sources & evidence

ORD record
ord-c739eb90c9e04fc3bb11bfa1d5c825e3
Source dataset
uspto-grants-2012_01
Patent number
US08106205B2

Reaction notes

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