Diisopropylethylamine → HCID 178422574, compound

HRID 1844265Notes

Reaction equation

HRID 1844265 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:11])[C:3]=1[N:12]=[C:13]=[S:14].Cl.[NH2:16][NH:17][C:18](N)=[NH:19].C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH2:19][C:18]1[N:12]([C:3]2[C:4]([CH3:11])=[CH:5][C:6]([CH:8]3[CH2:9][CH2:10]3)=[CH:7][C:2]=2[Cl:1])[C:13]([SH:14])=[N:16][N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59813078HCID 59813078, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178422574HCID 178422574, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Compound 3 (935 mg, 4.2 mmol) was dissolved in 5 mL of dimethylformamide, aminoguanidine hydrochloride salt (695 mg, 6.3 mmol) and diisopropyl ethylamine (1.1 mL, 6.3 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 (20 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-(2-chloro-4-cyclopropyl-6-methylphenyl)-4H-1,2,4-triazole-3-thiol (4). (780 mg, 66% yield)

Workup

  1. concentrationThe mixture was then concentrated and to the resulting residue
  2. additionwas added 2M aqueous sodium hydroxide solution (20 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-81e65ee02928460eae2c4f0eeea02ddb
Source dataset
uspto-grants-2015_02
Patent number
US08946273B2

Reaction notes

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