Isopropyl acetoacetate → HCID 9867306, compound

HRID 1656684Notes

Reaction equation

HRID 1656684 reaction equation
[C:1]1([C:7]2[S:8][C:9]3[C:15]([CH:16]=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:24][CH:25]([CH3:27])[CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=O.[NH2:28]/[C:29](/[CH3:33])=[CH:30]\[C:31]#[N:32]>C(O)C>[C:31]([C:30]1[CH:16]([C:15]2[C:9]3[S:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=[CH:13][CH:14]=2)[C:19]([C:18]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[C:20]([CH3:22])[NH:28][C:29]=1[CH3:33])#[N:32]

Participants

5

Reactant 3

HCID 68329Isopropyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 15676493HCID 15676493, compound

Product 1

HCID 9867306HCID 9867306, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 mmol of 2-phenyl-benzothiazole-7-carboxaldehyde, 10 mmol of isopropyl acetoacetate and 10 mmol of 3-aminocrotononitrile are boiled overnight in 20 ml of ethanol, the mixture is concentrated and the residue is purified on a silica gel column (cyclohexane/ethyl acetate=6:4) Yield: 28% of theory M.p.: 218° C.

Workup

  1. concentrationthe mixture is concentrated
  2. customthe residue is purified on a silica gel column (cyclohexane/ethyl acetate=6:4) Yield: 28% of theory M.p.: 218° C.

Sources & evidence

ORD record
ord-eab964e011ee42219dce04ab694de72d
Source dataset
uspto-grants-1993_10
Patent number
US05254692

Reaction notes

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