HCID 67843395, compound → HCID 14868519, compound

HRID 1646882Notes

Reaction equation

HRID 1646882 reaction equation
C([NH:8][C:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]=1[NH:18][C:19]([C:21]([O:23]CC)=O)=[O:20])(C(OCC)=O)=O>Cl>[NH:18]1[C:19](=[O:20])[C:21](=[O:23])[NH:8][C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]1=2

Participants

3

Reactant 1

HCID 67843395HCID 67843395, compound

Product 1

HCID 14868519HCID 14868519, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2,3-bis(ethoxalylamino)benzo[b]thiophene (5.47 g, 15 mmol) in 250 ml of 4 N hydrochloric acid was heated to reflux for 2 h. Then the mixture was cooled on an ice bath, and filtered. The crude product was washed with water and recrystallized from a mixture of ethanol, DMF and water with decolorizing charcoal. The recrystallized solid was filtered off, washed with ethanol and ether, and dried for 1 h at 100° C. to give 2.2 g (62%) of the pure title compound as a monohydrate; m.p. 377.6° C. DSC); 1R (KBr): 3200-2500, 1670 cm-1 ; 1H-NMR (DMSO-d6): δ 3.3 (broad s, 2H, H2O); 7.1-7.6 (m, 2H, ArH), 7.8-8.1 (m, 2H, ArH), 11.9-13.6 (broad, 2H, 2NH); MS (m/e): 218 (M+, 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureThen the mixture was cooled on an ice bath
  4. filtrationfiltered
  5. washThe crude product was washed with water
  6. customrecrystallized from a mixture of ethanol, DMF and water with decolorizing charcoal
  7. filtrationThe recrystallized solid was filtered off
  8. washwashed with ethanol and ether
  9. customdried for 1 h at 100° C.

Sources & evidence

ORD record
ord-ee44ed71735f48a199ec9b3ac13c1061
Source dataset
uspto-grants-1993_01
Patent number
US05182279

Reaction notes

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