Dichloromethane → HCID 178439215, compound

HRID 1869729Notes

Reaction equation

HRID 1869729 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(Cl)Cl>O>[CH:1]([C:4]1[CH:10]=[CH:9][C:7](/[N:8]=[CH:17]/[C:16]2[CH:15]=[CH:14][C:13]([C:12]([F:11])([F:21])[F:22])=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 74644-IsopropylanilineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 178439215HCID 178439215, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Isopropylaniline (5.5 ml, 40.2 mmol) was added to a vigorously stirred mixture of 4-(trifluoromethyl)benzaldehyde (5.5 ml, 40.2 mmol) in H2O (60 ml) at room temperature. After 2 hours, DCM (100 ml) was added and the mixture was stirred for 20 minutes. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated to give the imine (11.6 g, 99%) as a beige solid. 1H NMR (360 MHz, CDCl3) δ: 1.28 (6H, d, J 6.9), 2.95 (1H, septet, J 6.9), 7.18-7.21 (2H, m), 7.25-7.29 (2H, m), 7.71-7.73 (2H, m), 8.00-8.02 (2H, m), 8.52 (1H, s).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-e176fda56af54873816531e2ee8e271a
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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