Acetone → HCID 86638781, compound

HRID 1618869Notes

Reaction equation

HRID 1618869 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([CH:17]=O)[CH:14]=[CH:13][C:12]=1[NH2:19])[CH3:2].[C:21]([C:23]1[C:24](=[C:31]([C:34]#[N:35])[C:32]#[N:33])[O:25][C:26]([CH3:30])([CH3:29])[C:27]=1[CH3:28])#[N:22].C(Cl)(Cl)Cl.CC(C)=O>C(O)(=O)C.N1C=CC=CC=1.O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([CH:17]=[CH:28][C:27]2[C:26]([CH3:30])([CH3:29])[O:25][C:24](=[C:31]([C:32]#[N:33])[C:34]#[N:35])[C:23]=2[C:21]#[N:22])[CH:14]=[CH:13][C:12]=1[NH2:19])[CH3:2]

Participants

8

Reactant 4

HCID 180AcetoneHCID 6212ChloroformHCID 99903452-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrileHCID 59180880HCID 59180880, compound

Product 1

HCID 86638781HCID 86638781, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Acetic acid (5 drops) was added to a solution of 6-(2-amino-5-formyl-phenoxy)-hexanoic acid ethyl ester (0.310 g, 1.10 mmol) and 2-(3-cyano-4,5,5-trimethyl-5H-furan-2-ylidene)-malononitrile. (0.26 g, 1.33 mmol) in pyridine (10 ml). After stirring for 24 hours at room temperature, the mixture was diluted with 100 mls of water causing the formation of a dark purple precipitate which was removed by suction filtration and washed with water. The material, was found to be pure 6-{2-amino-5-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro furan-3-yl)-vinyl]phenoxy}-hexanoic acid ethyl ester by NMR (0.38 g, 75%). Small crystals of this product were obtained by pouring the NMR sample (chloroform) into a small amount of acetone and allowing this solution to slowly evaporate. Mp: 164.5° C. 1H NMR (400 MHz, CDCl3) δ: 7.58 (d, 1H, J=16 Hz), 7.17 (dd, 1H, J=8 Hz, J=1.6 Hz), 7.01 (d, 1H, J=1.6 Hz), 6.77 (d, 1H, J=16 Hz), 6.72 (d, 1H, J=8 Hz), 4.70 (s, 2H), 4.16 (q, 2H, J=7.2 Hz), 4.11 (t, 2H, J=6.2 Hz), 2.38 (t, 2H, J=7.2 Hz), 1.91 (m, 2H), 1.78 (s, 6H), 1.76 (m, 2H), 1.61 (m, 2H), 1.28 (t, 3H, 13C NMR (400 MHz, (CDCl3) δ: 176.06, 174.30, 173.59, 148.75, 146.35, 143.18, 126.97, 124.02, 113.85, 112.40, 111.65, 111.16, 110.20, 109.73, 96.99, 68.41, 60.35, 34.14, 28.78, 26.75, 25.65, 24.63, 14.26. IR (neat): 3461, 3341, 3251, 3215, 2987, 2946, 2873, 2360, 2219, 2208, 1728, 1630, 1587, 1549, 1521, 1482, 1448, 1415, 1357, 1335, 1273, 1235, 1211, 1187, 1166, 1145, 1108, 1028, 1013, 961, 946, 906, 871, 861, 828, 816, 805, 748.

Workup

  1. customwas removed by suction filtration
  2. washwashed with water
  3. customSmall crystals of this product were obtained
  4. customto slowly evaporate

Sources & evidence

ORD record
ord-dc162b33eb4d4291b0652c26b4e73f43
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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