Sodium Bicarbonate → HCID 178512547, compound

HRID 1461415Notes

Reaction equation

HRID 1461415 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[NH:18]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)[C:19]([NH2:21])=[NH:20].[C:31]([O-:34])([OH:33])=[O:32].[Na+]>N1C=CC=CC=1>[C:31](=[O:32])([OH:34])[OH:33].[NH:18]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([O:17][C:14]2[CH:13]=[CH:12][C:11]([S:10][CH2:9][CH2:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:16][CH:15]=2)=[O:27])=[CH:24][CH:23]=1)[C:19]([NH2:21])=[NH:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 140519404-Hydroxyphenyl 2-(tetrahydropyran-2-yloxy)ethyl sulfide2×HCID 178512519HCID 178512519, compound

Product 1

HCID 178512547HCID 178512547, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

96.08 g of 4-hydroxyphenyl 2-(tetrahydropyran-2-yloxy)ethyl sulfide synthesized by the above process (2) was dissolved in 800 m(of pyridine. 4-Guanidinobenzoyl chloride was added to the solution under cooling with ice and the mixture was stirred at room temperature for 24 h or longer. A saturated aqueous sodium hydrocarbonate solution was added thereto under cooling with ice and the precipitate thus obtained was recovered by filtration, washed with water, then acetone and finally ethyl acetate and dried to obtain 104 g of 4-(2-tetrahydropyran-2-yloxyethylthio)phenyl 4-guanidinobenzoate carbonate.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customthe precipitate thus obtained
  4. filtrationwas recovered by filtration
  5. washwashed with water
  6. dry with materialacetone and finally ethyl acetate and dried

Sources & evidence

ORD record
ord-3a416031e872428ba27a560e504393c7
Source dataset
uspto-grants-1991_12
Patent number
US05075335

Reaction notes

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