Sodium Iodide → 2-(3-{3-[2-Ethyl-5-hydroxy-4-(3h-imidazol-4-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acid hydrochloride

HRID 1008302Notes

Reaction equation

HRID 1008302 reaction equation
C[O:2][C:3](=[O:45])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28]CC3C=CC=CC=3)[C:25]([C:36](=O)[CH2:37][Cl:38])=[CH:24][C:23]=2[CH2:40][CH3:41])[C:12]=1[CH2:42][CH2:43][CH3:44].Cl.C(S[C:55](=[NH:57])[NH2:56])C1C=CC=CC=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)C>[ClH:38].[CH2:40]([C:23]1[CH:24]=[C:25]([C:36]2[NH:56][CH:55]=[N:57][CH:37]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:42][CH2:43][CH3:44])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:45])[CH3:41]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10852S-Benzylthiuronium chlorideHCID 11430Potassium CarbonateHCID 601111892-(3-{3-[5-Benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 102095352-(3-{3-[2-Ethyl-5-hydroxy-4-(3h-imidazol-4-yl)phenoxy]propoxy}-2-propyl-phenoxy)benzoic acid hydrochlorideYield 53.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-{3-[5-benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (800 mg, 1.27 mmol), 2-benzyl-2-thiopseudourea hydrochloride (313 mg, 1.52 mmol), sodium iodide (77 mg, 0.51 mmol), and potassium carbonate (700 mg, 5.06 mmol) in N,N-dimethylformamide (20 mL) was treated at 80° C. for 6 h. The mixture was cooled, diluted with diethyl ether, and washed once with water. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate/70% hexane) of the residue provided 376 mg (40%) of the title compound as a yellow amorphous solid. 1H NMR (CDCl3) δ 7.89 (d, J=8 Hz, 1H), 7.36 (m, 9H), 7.20 (m, 5H), 7.21 (d, J=9 Hz, 1H), 7.06 (d, J=8 Hz, 1H), 6.79 (d, J=8 Hz, 1H), 6.67 (d, J=8 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=8 Hz, 1H), 5.07 (s, 2H), 4.21 (t, J=6 Hz, 2H), 4.18 (t, J=6 Hz, 2H) , 4.10 (s, 2H), 3.83 (s, 3H), 2.63 (m, 4H), 2.31 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=7 Hz, 2H), 1.18 (t, J=8 Hz, 3H), 0.90 (t, J=7 Hz, 3H); TOF MS ES exact mass calculated for C45H47N2O6S (p+1): m/z=743.3155. Found: 743.3142; IR (CHCL3, cm−1) 2963, 1720, 1602, 1453. Anal. Calcd for C45H46N2O6S: C, 72.75; H. 6.24; N, 3.77. Found: C, 72.69; H, 6.17; N, 3.56.

Workup

  1. additionwas treated at 80° C. for 6 h
  2. temperatureThe mixture was cooled
  3. washwashed once with water
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cd5553abc4b44af8f5bfc72191a26f8
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

Loading…