4-Cyanobenzaldehyde → HCID 57762434, compound

HRID 1921126Notes

Reaction equation

HRID 1921126 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].O=[C:26]([CH3:31])[CH2:27][C:28]([NH2:30])=[O:29]>C1COCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:27]([C:28]([NH2:30])=[O:29])=[C:26]([CH3:31])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=3)[C:10](=[S:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 80077AcetoacetamideHCID 7358443-(Trifluoromethyl)phenylthiourea

Product 1

HCID 57762434HCID 57762434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Trifluoromethylphenyl thiourea (200 mg, 0.91 mmol), 4-cyanobenzaldehyde (238.2 mg, 1.82 mmol) and 3-oxobutanamide (183 mg, 1.82 mmol) are dissolved in 5 ml THF. Ethyl polyphosphate (0.30 g) is added and the reaction mixture is stirred at reflux temperature overnight. After cooling to room temperature, it is quenched with 10 ml of water and extracted with 10 ml ethyl acetate (2×). The combined organic layers are dried with sodium sulfate and the solvent is removed in vacuo. The product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

Workup

  1. temperatureat reflux temperature overnight
  2. customit is quenched with 10 ml of water
  3. extractionextracted with 10 ml ethyl acetate (2×)
  4. dry with materialThe combined organic layers are dried with sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

Sources & evidence

ORD record
ord-c0fe920d5242468cb72b2dd22d7d4eea
Source dataset
uspto-grants-2012_05
Patent number
US08173665B2

Reaction notes

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