Dichloromethane → HCID 67350634, compound

HRID 451635Notes

Reaction equation

HRID 451635 reaction equation
[CH:1]1([CH3:13])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([C:10](Cl)=[O:11])[CH2:2]1.N[C:15]1[CH:20]=[CH:19][C:18]([CH:21](CC)[C:22]([NH2:24])=[O:23])=C[CH:16]=1.C([N:29]([CH2:32][CH3:33])CC)C.[CH2:34](Cl)Cl>>[NH2:24][C:22](=[O:23])[CH2:21][CH2:18][CH2:19][C:20]1[CH:34]=[CH:33][C:32]([NH:29][C:10]([CH:3]2[CH2:2][C@H:1]([CH3:13])[CH2:6][CH2:5][C@H:4]2[CH:7]([CH3:9])[CH3:8])=[O:11])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-HCID 14451767HCID 14451767, compound

Product 1

HCID 67350634HCID 67350634, compound

Procedure

The p-Menthane-3-carboxylic acid chloride as a crude (13.6 mmol, 1 eq) was dissolved in anhydrous CH2Cl2 and add to the mixture of 4-aminophenylbutyramide (1.1 eq, 15.0 mmol, 2.67 g) and triethylamine (1.5 eq, 20.4 mmol, 2.1 g) cooled to 0 C. The reaction was allowed to warm to the RT and checking by GC. After 1 hour GC showed that reaction is completed. CH2Cl2 (50 mL) was added to the reaction and this mixture was washed by 0.1 N HCl aq, water, 0.1 N NaOH aq, by brine and dried over MgSO4. Filtrate and evaporate give white solid which was crystallized from hot ethyl acetate providing 3 g (65%) product as white solid. C21H32N2O2 (MW 344.24); 1H NMR (500 MHz, DMSO-d6) δ: 9.78 ppm (br. s, 1H); 7.49 ppm (d, 2H, J=8.40 Hz); 7.27 ppm (br. s, 1H); 7.09 ppm (d, 2H, J=8.40 Hz); 6.69 ppm (br. s, 1H); 2.50 ppm (t, 2H, J=7.70 Hz); 2.29 ppm (t, 1H, J=11.40 Hz, of d, J=3.17 Hz); 2.04 ppm (t, 2H, J=7.48 Hz); 1.69-1.78 ppm (m, 4H); 1.59-1.67 ppm (m, 2H); 1.51 ppm (t, 1H, J=11.56 Hz); 1.31-1.40 ppm (m, 1H); 1.14 ppm (q, 1H, J=12.14 Hz); 1.02 ppm (q, 1H, J=12.91 Hz); 0.89-0.96 ppm (m, 1H); 0.87 ppm (2d, 6H, J=6.94 Hz); 0.79 ppm (d, ˜83% of 3H, J=6.90 Hz); 0.75 ppm (d, ˜17% of 3H, J=6.90 Hz).

Workup

  1. temperaturecooled to 0 C
  2. customAfter 1 hour GC showed that reaction
  3. washthis mixture was washed by 0.1 N HCl aq, water, 0.1 N NaOH aq, by brine
  4. dry with materialdried over MgSO4
  5. customFiltrate and evaporate
  6. customgive white solid which
  7. customwas crystallized from hot ethyl acetate providing 3 g (65%) product as white solid

Sources & evidence

ORD record
ord-45cec9c71ac54a4895f4359001930222
Source dataset
uspto-grants-2013_07
Patent number
US08487130B2

Reaction notes

Loading…