Diphenylmethylidenehydrazine → HCID 76571888, compound

HRID 2111231Notes

Reaction equation

HRID 2111231 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][N:8]([CH3:10])[CH3:9])[S:4][C:3]=1[CH:11]=O.[C:13](=[N:26][NH2:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:13](=[N:26][N:27]=[CH:11][C:3]1[S:4][C:5]([CH2:7][N:8]([CH3:10])[CH3:9])=[CH:6][C:2]=1[Br:1])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 79304DiphenylmethylidenehydrazineHCID 57637280HCID 57637280, compound2×

Product 1

HCID 76571888HCID 76571888, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To 3-bromo-5-dimethylaminomethyl-thiophene-2-carbaldehyde [4.30 g, 17.3 mmol, Intermediate (2)] in ethanol (40 mL) is added benzophenone hydrazone (3.75 g, 19.0 mmol). The solution was heated at 65° C. for 5 hours. The solvent is removed under reduced pressure. The residue is chromatographed through silica gel (n-heptane-ethyl acetate. 90:10 as eluant) to produce [5-(Benzhydrylidene-hydrazonomethyl)-4-bromo-thiophen-2-ylmethyl]-dimethyl-amine] 5.57 g, 75%, Intermediate (3)] as an orange oil. LC/MS: RT=2.72 minutes, 426.05 m/e (M+H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is chromatographed through silica gel (n-heptane-ethyl acetate. 90:10 as eluant)

Sources & evidence

ORD record
ord-c70d39e45d51460e9a1d96cb75fc35b6
Source dataset
uspto-grants-2009_04
Patent number
US07518000B2

Reaction notes

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