Ammonium Chloride → HCID 86759583, compound

HRID 2308121Notes

Reaction equation

HRID 2308121 reaction equation
[CH3:1][O:2][C:3]1[CH:66]=[C:65]([CH:67]=[CH:68][C:69]([O:71][CH3:72])=[O:70])[CH:64]=[CH:63][C:4]=1[O:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:47]=[CH:46][C:45]([O:48][C:49](=[O:62])[C:50]2[CH:55]=[CH:54][C:53]([CH:56]=[CH:57][C:58]([O:60][CH3:61])=[O:59])=[CH:52][CH:51]=2)=[CH:44][C:14]=1[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:43])[C:31]1[CH:36]=[C:35]([N+:37]([O-])=O)[CH:34]=[C:33]([N+:40]([O-])=O)[CH:32]=1)=[O:16].[Cl-].[NH4+]>[Zn].CO.O>[CH3:1][O:2][C:3]1[CH:66]=[C:65]([CH:67]=[CH:68][C:69]([O:71][CH3:72])=[O:70])[CH:64]=[CH:63][C:4]=1[O:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:47]=[CH:46][C:45]([O:48][C:49](=[O:62])[C:50]2[CH:51]=[CH:52][C:53]([CH:56]=[CH:57][C:58]([O:60][CH3:61])=[O:59])=[CH:54][CH:55]=2)=[CH:44][C:14]=1[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:43])[C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[C:33]([NH2:40])[CH:32]=1)=[O:16]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86759584HCID 86759584, compound

Product 1

HCID 86759583HCID 86759583, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22242641Methanol--water (1/1)Solvent2×

Procedure

0.997 g (1.00 mmol) 3,5-Dinitrobenzoic acid 11-[2-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]benzoyloxy]undecyl ester and 0 g (4.00 mmol) of ammonium chloride were suspended in 15 ml of a mixture consisting of methanol:water 9:1. 1.31 g (20.0 mmol) of zinc was then added in one portions. After 0.5 hour at room temperature 20 ml of a mixture consisting of methanol:water 9:1 is added to the thick suspension. After a further 21 hours the reaction suspension was partitioned between dichloromethane and water. The resulting suspension was filtered, the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water. The organic phase was then dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography of the residue on silica yield 3,5-Diaminobenzoic acid 11-[2-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]benzoyloxy]undecyl ester.

Workup

  1. additionis added to the thick suspension
  2. customAfter a further 21 hours the reaction suspension was partitioned between dichloromethane and water
  3. filtrationThe resulting suspension was filtered
  4. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d13574d31dda41258e04044c1565a2e3
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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