Dichloromethane → HCID 18794266, compound

HRID 1004070Notes

Reaction equation

HRID 1004070 reaction equation
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(C)(C)C.Cl.CN(C)[CH2:24][CH2:25][CH2:26]N=C=NCC.[CH2:33](Cl)Cl>CN(C1C=CN=CC=1)C>[C:25]([C:18]1[CH:17]=[CH:16][C:15]([NH:14][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])=[CH:20][CH:19]=1)([CH3:26])([CH3:33])[CH3:24]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57096144,4,4-Trifluorocrotonic acid

Product 1

HCID 18794266HCID 18794266, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of 4,4,4-trifluorocrotonic acid (300 mg, 1.90 mmole), t-butylaniline (371 μL, 2.28 mmole), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (510 mg, 2.66 mmole) and DMAP (8 mg) in CH2Cl2 (5 mL) was stirred at room temperature for 18 hrs. The mixture was diluted with CH2Cl2, washed with 1N NaOH, water, 1N HCl, 10% NaHCO3 and dried (MgSO4). Evaporation in vacuo to gave the title compound as a white solid. NMR (CDCl3): δ 1.33 (s, 9H); 6.63 (d, 1H); 6.90 (dq, 1H); 7.37 (s, 1H); 7.39 (d, 2H); 7.51 (d, 2H).

Workup

  1. washwashed with 1N NaOH, water, 1N HCl, 10% NaHCO3
  2. dry with materialdried (MgSO4)
  3. customEvaporation in vacuo

Sources & evidence

ORD record
ord-89b7aeefaf2d45199f9c147b785be2b9
Source dataset
uspto-grants-2000_04
Patent number
US06048869

Reaction notes

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