1,5-Dibromopentane → HCID 70055769, compound

HRID 1977311Notes

Reaction equation

HRID 1977311 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[N:17]([CH:18]=2)[N:16]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[S:14]3)=[CH:7][CH:6]=1)C.[C:27](=[O:30])([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:3][C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[N:17]([CH:18]=2)[N:16]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:30][CH3:27])=[CH:23][CH:24]=2)[S:14]3)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 81001,5-DibromopentaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 136386398HCID 136386398, compound

Product 1

HCID 70055769HCID 70055769, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-[2-(4-hydroxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid ethyl ester (1 g) and potassium carbonate (4 g) in N,N-dimethylformamide (50 ml) was added 1,5-dibromopentane (2 ml) and the mixture was stirred at room temperature for 6 hours. The reaction mixture was pulverized with ethyl acetate. The precipitate was collected by filtration, washed with water and methanol. To a suspension of the powder in methanol (10 ml) was added sodium methylate (28% in methanol) (20 ml) and the mixture was stirred at 80° C. for 19 hours. The reaction mixture was pulverized with water. The precipitate was collected by filtration, washed with water, methanol and diisopropyl ether and dried to give 4-[2-[4-(5-methoxypentyloxy)phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid methyl ester (479 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and methanol
  3. additionTo a suspension of the powder in methanol (10 ml)
  4. additionwas added sodium methylate (28% in methanol) (20 ml)
  5. stirringthe mixture was stirred at 80° C. for 19 hours
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water, methanol and diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-b87cc644afc4491a8d9fff1fec3fe825
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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