Dimethylformamide → HCID 178487445, compound

HRID 448156Notes

Reaction equation

HRID 448156 reaction equation
Br[C:2]1[N:3]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH:32]3CC3)=[CH:24][CH:23]=2)[C:4]([S:7]CC(NC2C=CC(C(O)=O)=CC=2Cl)=O)=[N:5][N:6]=1.Cl.NNC(N)=N.C([N:44](C(C)C)CC)(C)C.CN(C)[CH:52]=[O:53]>>[NH2:44][C:2]1[N:3]([C:22]2[C:27]3[C:26](=[CH:31][CH:30]=[C:29]([O:53][CH3:52])[CH:28]=3)[C:25]([CH3:32])=[CH:24][CH:23]=2)[C:4]([SH:7])=[N:5][N:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 16221816Rdea806HCID 178418668HCID 178418668, compound

Product 1

HCID 178487445HCID 178487445, compoundYield 91%

Conditions

Temperature
50 °C

Procedure

Compound 7 (1.0 g, 4.4 mmol) was dissolved in 10 mL of dimethylformamide, aminoguanidine hydrochloride salt (723 mg, 6.5 mmol) and diisopropyl ethylamine (1.14 mL, 6.5 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-(7-methoxy-4-methylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (8). (1.14 mg, 91% 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-f7c7e917dff942adbbe0db86a0f80fbe
Source dataset
uspto-grants-2013_07
Patent number
US08481581B2

Reaction notes

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