Water → HCID 22713195, compound

HRID 351557Notes

Reaction equation

HRID 351557 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH2:11]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]3=[N:28][C:29]([C:31]4[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=4)=[CH:30][N:25]3[N:24]=2)=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH2:14][CH3:15].O>ClCCl>[CH2:11]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[S:27][C:26]3=[N:28][C:29]([C:31]4[CH:32]=[CH:33][C:34]([C:35]([O:1][N:2]5[C:6]6[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=6[N:4]=[N:3]5)=[O:36])=[CH:38][CH:39]=4)=[CH:30][N:25]3[N:24]=2)=[CH:21][CH:22]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 22494600HCID 22494600, compound

Product 1

HCID 22713195HCID 22713195, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-hydroxybenzotriazole (1.67 g) and 4-[2-(4-pentyloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-benzoic acid (4.2 g) in dichloromethane (170 ml) was added 1-ethyl-3-(31-dimethylaminopropyl)carbodiimide hydrochloride (WSCD.HCl) (2.95 g) and stirred for 6 hours at ambient temperature. The reaction mixture was added to water. The organic layer was taken and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-[4-[2-(4-pentyloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-benzoyloxy]benzotriazole (2.456 g).

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationMagnesium sulfate was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59e2997b00fc4030aa479c380bcd479a
Source dataset
uspto-grants-2004_06
Patent number
US06743776B2

Reaction notes

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