Acetic Acid → HCID 136383527, compound

HRID 732931Notes

Reaction equation

HRID 732931 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[N:17]([CH2:18][CH:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]=[CH:15][C:14]=1[C:27]([O:29]CC)=O)=[S:11])(=O)C1C=CC=CC=1.C(O)(=O)C>[OH-].[Na+].O>[OH:26][CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][N:17]1[C:13]2[NH:12][C:10](=[S:11])[NH:9][C:27](=[O:29])[C:14]=2[CH:15]=[N:16]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86609906HCID 86609906, compound

Product 1

HCID 136383527HCID 136383527, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6 (4.38 g, 10 mmol) in 2 M NaOH (40 mL) was refluxed for 10 min and successively diluted with H2O (40 mL). The solution was acidified with glacial acetic acid. Standing in a refrigerator for 12 h, a solid crystallized, and was filtered and recrystallized from absolute ethanol to give 7 (2.3 g, 80%) as a white solid; mp 264-265° C. 1H NMR: δ 4.15-4.30 and 4.55-4.72 (2m, 2H, CH2N), 4.85-5.00 (m, 1H, CHO), 5.66 (br s, 1H, OH, disappears with D2O), 7.20-7.51 (m, 5H Ar), 8.02 (s, 1H, H-3), 12.20 (s, 1H, NH, disappears with D2O), 13.40 (s, 1H, NH, disappears with D2O). IR cm−1: 3362 (NH), 3142-2773 (OH), 1681 (CO). Anal. (C13H12N4O2S) C, H, N, S.

Workup

  1. customa solid crystallized
  2. filtrationwas filtered
  3. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-7c2de85b7bf1413ab5a66d9f2c8636c8
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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