Magnesium Carbonate → HCID 9828518, compound

HRID 1008303Notes

Reaction equation

HRID 1008303 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)=[CH:24][C:23]=2[CH2:40][CH3:41])[C:12]=1[CH2:42][CH2:43][CH3:44].[CH:46]([NH2:48])=[S:47].C(=O)([O-])[O-].[Mg+2]>O1CCOCC1.C(OCC)C.[OH-].[Na+]>[CH2:40]([C:23]1[CH:24]=[C:25]([C:36]2[N:48]=[CH:46][S:47][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 3

HCID 11029Magnesium CarbonateHCID 3005587MethanethioamideHCID 601111892-(3-{3-[5-Benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 9828518HCID 9828518, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(3-{3-[5-benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (500 mg, 0.792 mmol), thioformamide (20 mL, 8.0 mmol), and magnesium carbonate in dioxane (10 mL) was heated at reflux for 2 h. The mixture was cooled to room temperature and diluted with diethyl ether and 0.2 M sodium hydroxide solution. The organic layer was separated, washed with saturated sodium chloride solution, dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 10% ethyl acetate/90% hexane) of the residue provided 254 mg (50%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.91 (s, 1H), 8.11 (s, 1H), 7.87 (dd, J=8, 1 Hz, 1H), 7.84 (d, J=1 Hz, 1H), 7.40 (m, 6H), 7.08 (m, 2H), 6.80 (d, J=8 Hz, 1H), 6.68 (d, J=8 Hz, 1H), 6.62 (s, 1H), 6.43 (d, J=8 Hz, 1H), 5.16 (s, 2H), 4.21 (t, J=6 Hz, 4H), 3.83 (s, 3H), 2.68 (m, 4H), 2.32 (quintet, J=6 Hz, 2H), 1.56 (hextet, J=8 Hz, 2H), 1.21 Ct, J=7 Hz, 3H), 0.90 (t, J=7 Hz, 3H); TOF MS ES+ exact mass calculated for C38H40NO6S (p+1): m/z=638.2576. Found: 638.2579. IR (CHCl3, cm−1) 2964, 1719, 1563, 1461.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f960dac0415b4439958a6ef853782434
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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