Methyl Anthranilate → HCID 178497648, compound

HRID 2119028Notes

Reaction equation

HRID 2119028 reaction equation
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[C:16]([O:25][CH3:26])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:19].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.N1C=CC=CC=1>[ClH:1].[CH3:26][O:25][C:16]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][NH:2][C:3]([NH2:5])=[NH:4])[CH2:12][CH2:11]1)=[O:15])=[O:24]

Participants

6

Reactant 3

HCID 8635Methyl AnthranilateHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, compound

Product 1

HCID 178497648HCID 178497648, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (111 g, 0.5 mole) (which is prepared by the method as disclosed in Japanese Patent First Publication No. 19694/1977, C.A., 87, 53269x) and methyl anthranilate (75.6 g, 0.5 mole) are dissolved in a mixture of dimethylformamide and pyridine (1:1, 1250 ml), and thereto is added dicyclohexylcarbodiimide (103 g, 0.5 mole), and the mixture is stirred at room temperature for 40 hours. After the undissolved materials are filtered off, the solvent is evaporated under reduced pressure. To the residue are added methanol (500 ml) and water (80 ml), and the mixture is stirred, and the undissolved materials are again filtered off and the solvent is evaporated under reduced pressure. The resulting residue is washed with acetone (2000 ml) and recrystallized from water to give the title compound (143 g) as white crystals. The physical data of this compound are identical with those of N-(o-methoxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride prepared in Example 2.

Workup

  1. filtrationAfter the undissolved materials are filtered off
  2. customthe solvent is evaporated under reduced pressure
  3. additionTo the residue are added methanol (500 ml) and water (80 ml)
  4. stirringthe mixture is stirred
  5. filtrationthe undissolved materials are again filtered off
  6. customthe solvent is evaporated under reduced pressure
  7. washThe resulting residue is washed with acetone (2000 ml)
  8. customrecrystallized from water

Sources & evidence

ORD record
ord-f2f28c7b4cfd44d38ede490c8a516dcf
Source dataset
uspto-grants-1987_07
Patent number
US04681895

Reaction notes

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