Ethanol → DW-1350

HRID 732248Notes

Reaction equation

HRID 732248 reaction equation
[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:30]=[CH:29][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].C(O)C.Cl.[NH2:35][OH:36].C(N(CC)CC)C>O>[OH:36][NH:35][C:25](=[NH:26])[C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:13]2[CH:29]=[CH:30][C:10]([C:5]3[N:6]=[C:7]([CH3:9])[S:8][C:4]=3[CH:1]([CH3:2])[CH3:3])=[CH:11][CH:12]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 162024464-{5-[4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenoxy]-Pentoxy}-Benzonitrile

Product 1

HCID 178432563DW-1350Yield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

While 45 g of 4-5-[4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenoxy]-pentoxy-benzonitrile (10) prepared in Example 6 were added to 300 ml of ethanol and stirred, 15 g of hydroxylamine hydrochloride and 30 ml of triethylamine were added. The temperature was gradually increased and stirring under reflux was continued for 15 hr. After the reaction was completed, the temperature was decreased to 40° C., and the resultant reaction solution was slowly added with water, thereby being crystallized. The precipitated solid was filtered and washed with water, thus obtaining 44.2 g (yield: 95%) of a title compound as a white solid.

Workup

  1. temperatureThe temperature was gradually increased
  2. stirringstirring
  3. temperatureunder reflux
  4. customwas decreased to 40° C.
  5. customthe resultant reaction solution
  6. custombeing crystallized
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-1399806e59e64f8f8ec64ab6507d2a36
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Reaction notes

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