5-Aminosalicylic Acid → HCID 12270301, compound

HRID 1579908Notes

Reaction equation

HRID 1579908 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)=O.[NH2:16][C:17]1[CH:25]=[C:21]([C:22]([OH:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1>C(O)C>[C:22]([C:21]1[CH:25]=[C:17]([N:16]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[CH:8]=[C:6]2[C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:19][C:20]=1[OH:26])([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 12270336HCID 12270336, compound

Product 1

HCID 12270301HCID 12270301, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.22 g. (0.01 mole) of 2-(2-thienoylmethyl)cyclohexanone, (1.53 g. (0.01 mole) of 5-aminosalicylic acid, and 25 ml. of ethanol was heated uder reflux under nitrogen for 4 hours and filtered. The filtrate was concentrated to an oil which solidified when triturated with petroleum ether. Recrystallization from acetonitrile gave 1.0 g. (29%) of yellow crystals, m.p. 211°-213°.

Workup

  1. additionA mixture of 2.22 g
  2. temperatureuder reflux under nitrogen for 4 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to an oil which
  5. customtriturated with petroleum ether
  6. customRecrystallization from acetonitrile
  7. customgave 1.0 g

Sources & evidence

ORD record
ord-9a750dc0f4a14b8f93da8b371278c901
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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