Ammonium Chloride → HCID 21697275, compound

HRID 378977Notes

Reaction equation

HRID 378977 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C.[Cl:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34]([Cl:37])[C:35]=1[CH3:36].[CH:38]1([O:43][C:44]2[C:45]([N+:54]([O-:56])=[O:55])=[C:46]([CH:49]=[CH:50][C:51]=2[O:52][CH3:53])[CH:47]=[O:48])[CH2:42][CH2:41][CH2:40][CH2:39]1.[NH4+].[Cl-]>O1CCCC1.O>[CH:38]1([O:43][C:44]2[C:45]([N+:54]([O-:56])=[O:55])=[C:46]([CH:47]([OH:48])[CH2:1][CH2:36][C:35]3[C:34]([Cl:37])=[CH:33][N:32]=[CH:31][C:30]=3[Cl:29])[CH:49]=[CH:50][C:51]=2[O:52][CH3:53])[CH2:39][CH2:40][CH2:41][CH2:42]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 109538273,5-Dichloro-4-methylpyridineHCID 21697271HCID 21697271, compoundHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 21697275HCID 21697275, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-75 °C

Procedure

A 2M solution under nitrogen of lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (47 ml, 94.9 mmoles) in dry tetrahydrofuran (100 ml) was added with 3,5-dichloro-4-methyl-pyridine (14.6 g, 90.4 mmoles), obtained as described in example 15, in dry tetrahydrofuran (100 ml), keeping the temperature under −65° C. At the end of the addition the mixture was left under stirring for 1 hour at −75° C., then added with 3-cyciopentyloxy-4-methoxy-2-nitro-benzaldehyde (24 g, 90.4 mmoles), obtained as described in example 28, in dry tetrahydrofuran (100 ml), keeping the temperature under −68° C. At the end of the addition the mixture was left under stirring for 1.5 hours at −72° C., then treated with NH4Cl (200 ml), heated to room temperature, diluted with water. The aqueous phase was twice extracted in ethyl acetate. The organic phases were discoloured with charcoal, anhydrified and dried under vacuum. The residue was tritured with isopropyl ether to give 4.76 g of the title product (yield: 84%).

Workup

  1. customobtained
  2. customunder −65° C
  3. additionAt the end of the addition the mixture
  4. waitwas left
  5. customobtained
  6. customunder −68° C
  7. additionAt the end of the addition the mixture
  8. waitwas left
  9. stirringunder stirring for 1.5 hours at −72° C.
  10. temperatureheated to room temperature
  11. extractionThe aqueous phase was twice extracted in ethyl acetate
  12. customdried under vacuum

Sources & evidence

ORD record
ord-7f1536c97a5c4276a04812dfda255a81
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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