Ethanol → HCID 12834425, compound

HRID 2285920Notes

Reaction equation

HRID 2285920 reaction equation
Br.NN=[CH:4][S:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21]CS(OC1C=CC(C)=CC=1)(=O)=O.C(O)C.[OH-].[Na+]>O.C(O)(=O)C>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][CH2:4][S:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20485167HCID 20485167, compoundHCID 70533063HCID 70533063, compound

Product 1

HCID 12834425HCID 12834425, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture containing 7.2 grams of 4-(((aminoiminomethyl)thio)methyl)benzoic acid monohydrobromide (0.025 mole), 7.1 grams of 4-methylphenyl 2-thiopheneethanesulfonate (0.025 mole), 50 ml of ethanol, 25 ml of 20% sodium hydroxide in water, and 25 ml of water were warmed to approximately 50° C. The orange solution obtained was mixed with 1 liter of ice-water and acidified with glacial acetic acid giving a pink solid. The pink solid was collected and recrystallized from acetonitrile to give the final product 4-(((2-(2-thienyl)ethyl)thio)methyl)benzoic acid as a pale pink solid having a melting point of 136°-137° C.

Workup

  1. customThe orange solution obtained
  2. customThe pink solid was collected
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-fb846d61edb349f596fd85f8e2efc1f4
Source dataset
uspto-grants-1982_04
Patent number
US04325959

Reaction notes

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