Hydrochloric Acid → HCID 15100255, compound

HRID 2253605Notes

Reaction equation

HRID 2253605 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[CH:23]1.Cl>O>[CH3:21][N:22]1[CH:26]=[C:25]([S:27]([NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=2)(=[O:29])=[O:28])[N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 3043419HCID 3043419, compound

Product 1

HCID 15100255HCID 15100255, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

6.3 g (32 mmol) of 4-(2-aminoethyl)phenoxyacetic acid are added to a solution of 9.7 g (79 mmol) of potassium carbonate in 50 ml of water and the mixture is stirred for 5 minutes. A suspension of 5.8 g (32 mmol) of 1-methyl-4-imidazolesulfonyl chloride from Example C-1 in 20 ml of water is slowly added to this suspension. The mixture is heated to 80° C. and stirred at this temperature for 2 hours. After cooling to room temperature, the reaction solution is acidified to pH 4 using 2N hydrochloric acid. The precipitate deposited is separated off, washed several times with water and recrystallized from dilute acetic acid in order to give the title compound of melting point 203°-204° C.

Workup

  1. additionis slowly added to this suspension
  2. stirringstirred at this temperature for 2 hours
  3. temperatureAfter cooling to room temperature
  4. customThe precipitate deposited is separated off
  5. washwashed several times with water
  6. customrecrystallized from dilute acetic acid in order

Sources & evidence

ORD record
ord-7211b65da0d84ca68d93e23b7d303059
Source dataset
uspto-grants-1993_08
Patent number
US05232922

Reaction notes

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