Methyl chloroacetate → Methyl 2-((5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate

HRID 38751Notes

Reaction equation

HRID 38751 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH2:7][C:8]1[N:9]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[C:10]([SH:13])=[N:11][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:7][C:8]1[N:9]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]3[CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[C:10]([S:13][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[N:11][N:12]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 178509206HCID 178509206, compound

Product 1

HCID 59763691Methyl 2-((5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-chloroacetate (0.73 mL, 8.3 mmol) was added dropwise over 5 min to a suspension of 5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol (2.24 g, 7.9 mmol) and potassium carbonate (1.21 g, 8.7 mmol) in DMF (40 mL) at room temperature. The reaction was stirred at room temperature for 24 h and slowly poured into a stirred ice-cold water solution. The tan precipitate was collected by vacuum filtration and dried under high vacuum at 50° C. for 16 h in the presence of P2O5 to yield methyl 2-(5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetate (2.24 g, 80%).

Workup

  1. filtrationThe tan precipitate was collected by vacuum filtration
  2. dry with materialdried under high vacuum at 50° C. for 16 h in the presence of P2O5

Sources & evidence

ORD record
ord-83043b28a00a419a9236279fc9ba1b55
Source dataset
uspto-grants-2013_09
Patent number
US08524754B2

Reaction notes

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