Sodium Acetate → HCID 90017823, compound

HRID 1054995Notes

Reaction equation

HRID 1054995 reaction equation
Cl[CH:2](Cl)[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:6]=[C:5]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:4]=1.ClC(Cl)C1N=C(N2CCCC2)N(CC2C=CC([O:42]C)=CC=2)N=1.C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:7]2[C:3]([CH:2]=[O:42])=[N:4][C:5]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:6]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 90026187HCID 90026187, compoundHCID 90026453HCID 90026453, compound

Product 1

HCID 90017823HCID 90017823, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 5-(dichloromethyl)-1-(4-methoxybenzyl)-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole and 3-(dichloromethyl)-1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazole from the previous step (299 mg, 0.876 mmol, Eq: 1) was suspended in ethanol (5 ml) and water (5 ml). Sodium acetate (180 mg, 2.2 mmol, Eq: 5) was added. The reaction mixture was heated for 16 h at 60° C. The mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate. The product (74 mg, 29%) was obtained as a yellow solid by column chromatography (SiO2, ethyl acetate n-heptane). MS: m/z=287.3 (M+H+)

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-a798d24309f14eb28c6b177d79327018
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…