(2Z)-3-Amino-2-butenenitrile → HCID 24800075, compound

HRID 1951557Notes

Reaction equation

HRID 1951557 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[S:13]1[C:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=2[N:15]=[C:14]1[CH2:22][C:23]([CH3:25])=O.[NH2:26]/[C:27](/[CH3:31])=[CH:28]\[C:29]#[N:30]>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:22]([C:14]3[S:13][C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=4[N:15]=3)=[C:23]([CH3:25])[NH:26][C:27]([CH3:31])=[C:28]2[C:29]#[N:30])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 131623961-(4,5,6,7-Tetrahydro-1,3-benzothiazol-2-yl)propan-2-oneHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 24800075HCID 24800075, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.931 mmol) of the compound from example 3A, 181 mg (0.931 mmol) of the compound from example 19A and 76 mg (0.931 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is taken up in 3 ml of ethyl acetate. The crystallizing solid is removed by filtration. The precipitate obtained in this way is washed with hot acetonitrile and dried under high vacuum. 131 mg (35% of theory) of the title compound are obtained.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. customThe crystallizing solid is removed by filtration
  3. customThe precipitate obtained in this way
  4. washis washed with hot acetonitrile
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-c1e015d355164bc8a72f78c68331fc20
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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