Hydrochloric Acid → HCID 131712377, compound

HRID 1577510Notes

Reaction equation

HRID 1577510 reaction equation
[CH3:1][NH2:2].O=C1C2C(=CC=CC=2)C(=O)[N:5]1[CH2:14][CH2:15][S:16][CH2:17][C:18]1[O:22][C:21]([C:23](OC)=[O:24])=[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=1.C[O-].[Na+].[ClH:36]>CO>[ClH:36].[NH2:5][CH2:14][CH2:15][S:16][CH2:17][C:18]1[O:22][C:21]([C:23]([NH:2][CH3:1])=[O:24])=[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 131712378HCID 131712378, compound

Product 1

HCID 131712377HCID 131712377, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Gaseous methylamine was passed into a solution of 5-[[2-(1,3-dioxo-2H-isoindol-2-yl)ethyl]thio]methyl-3-phenyl-2-furancarboxylic acid, methyl ester (4 g) and sodium methoxide (0.01 g) in dry methanol (50 ml). After 4 hours 2 M hydrochloric acid (100 ml) was added and the solution was extracted with diethyl ether (200 ml). The aqueous fraction was basified with 5 M sodium hydroxide (40 ml) and extracted with chloroform (200 ml). The chloroform extract was mixed with 2 M hydrochloric acid (100 ml) and the resulting solid was collected by filtration affording the title compound (1.6 g) as yellow needles. m.p. 189°-190°.

Workup

  1. extractionthe solution was extracted with diethyl ether (200 ml)
  2. extractionextracted with chloroform (200 ml)
  3. extractionThe chloroform extract
  4. additionwas mixed with 2 M hydrochloric acid (100 ml)
  5. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-d6b5a206494d4e29a7e1a5239bd22db8
Source dataset
uspto-grants-1981_09
Patent number
US04288443

Reaction notes

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