Ethyl 2-chloroacetoacetate → HCID 178432410, compound

HRID 844964Notes

Reaction equation

HRID 844964 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][N:3]=1.[Cl:15][CH:16]([C:22]([CH3:24])=O)[C:17](OCC)=[O:18]>C(O)(=O)C>[CH2:8]([S:7][C:5]1[N:6]=[C:2]2[N:1]=[C:22]([CH3:24])[C:16]([Cl:15])=[C:17]([OH:18])[N:3]2[N:4]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 178509291HCID 178509291, compound

Product 1

HCID 178432410HCID 178432410, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 16 g (77 mmol) of 3-amino-5-benzylthio-1,2,4-triazole and 10.6 g (77 mmol) of ethyl 2-chloroacetoacetate in 150 ml of glacial acetic acid was heated at 100° C. for 17 hours. Upon cooling to room temperature the solid which separated was collected by filtration. The filtrate was diluted with ice water to separate an additional quantity of solid. The solids were combined and dried to yield 14.0 g (60%) of the desired product as a solid, m.p. 258°-260° C. IR and 1H NMR were in agreement with the assigned structure.

Workup

  1. customseparated
  2. filtrationwas collected by filtration
  3. additionThe filtrate was diluted with ice water
  4. customto separate an additional quantity of solid
  5. customdried

Sources & evidence

ORD record
ord-06f654b291ff42f3ab1f1fe7b24f58bb
Source dataset
uspto-grants-1988_07
Patent number
US04755212

Reaction notes

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