Ethanol → HCID 19611365, compound

HRID 1602503Notes

Reaction equation

HRID 1602503 reaction equation
O.NN.[C:4]([C:8]1[N:9]=[C:10]([CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:54]=[CH:55][CH:56]=2)[C:18]([NH:20][C:21]2[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][S:44]([C:47]3[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[CH:38]=[CH:37][C:22]=2[O:23][CH2:24][CH2:25][N:26]2C(=O)C3=CC=CC=C3C2=O)=[O:19])[S:11][CH:12]=1)([CH3:7])([CH3:6])[CH3:5].C(O)C>O1CCCC1>[C:4]([C:8]1[N:9]=[C:10]([CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:54]=[CH:55][CH:56]=2)[C:18]([NH:20][C:21]2[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][S:44]([C:47]3[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=3)(=[O:45])=[O:46])[CH:38]=[CH:37][C:22]=2[O:23][CH2:24][CH2:25][NH2:26])=[O:19])[S:11][CH:12]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 19611385HCID 19611385, compound

Product 1

HCID 19611365HCID 19611365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, hydrazine monohydrate (190 μl, 3.8 mmol) was added to a mixture of N-[2-[2-[3-[(4-tert-butyl-2-thiazolyl)methoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxy]ethyl]phthalimide (1.5 g, 1.9 mmol), ethanol (5 ml) and tetrahydrofuran (20 ml), and the resulting mixture was stirred overnight at room temperature and then heated under reflux for 3 hours. Ice-water was added to the reaction solution, and then the product formed was extracted with chloroform. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and distilled water in that order, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was purified by silica gel column chromatography (eluent=chloroform:acetone=2:1), made into hydrochloride by adding 4 N hydrochloric acid/ethyl acetate, and then crystallized from diethyl ether to give 3-[(4-tert-butyl-2-thiazolyl)methoxy]-5'-[3-(4-chlorophenylsulfonyl)-propyl]-2'-(2-aminoethoxy)benzanilide 1.4 hydrochloride.0.7 hydrate (160 mg, 0.23 mmol, 12%) as white crystals.

Workup

  1. temperatureUnder ice-cooling
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. customthe product formed
  5. extractionwas extracted with chloroform
  6. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution
  7. distillationdistilled water in that order
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe resulting residue was purified by silica gel column chromatography (eluent=chloroform:acetone=2:1)
  11. additionby adding 4 N hydrochloric acid/ethyl acetate
  12. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-60312abe3a9e4eb6843527f865b2872c
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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