Acetic Acid → HCID 20605631, compound

HRID 481067Notes

Reaction equation

HRID 481067 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:16]2[C:15]3[N:11]([CH:12]=[CH:13][N:14]=3)[CH2:10][CH2:9][C:8]=2[N:7](CCC2C=CC([N+]([O-])=O)=CC=2)[CH:6]=1)=[O:4].[H-].[Na+].C(Cl)(Cl)Cl.C(O)(=O)C>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3]([C:5]1[C:16]2[C:15]3[N:11]([CH:12]=[CH:13][N:14]=3)[CH2:10][CH2:9][C:8]=2[NH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 24758Sodium hydrideHCID 20605627HCID 20605627, compound

Product 1

HCID 20605631HCID 20605631, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[2-(4-Nitro-phenyl)-ethyl]-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid methyl ester (19.67 mmol) in 100 mL DMF is treated with sodium hydride (60%, 1.97 g, 49.18 mmol) portion wise. The reaction is complete in about 2 h at 20° C. Chloroform is added and the reaction mixture is cooled to 5° C. before the dropwise addition of acetic acid (3.15 mL, 55.08 mmol) until pH of 1-3. A saturated solution of aqueous KHCO3 (150 mL) is added, stirred and separated. The separated organic phase is washed with water twice. The filtrate is concentrated directly. Most of the DMF is removed by high vacuum to give a brown wet solid. The wet solid is cooled to room temp. Ether is added, stirred, and filtered to give a brown solid which is dried in air overnight to give 5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid methyl ester, 9.11 g, (77%): 1H NMR (CD3OD) 3.05 (t, 2H), 3.86 (s, 3H), 4.25 (t, 2H), 6.97 (s, 1H), 7.05 (s, 1H), 7.40 (s, 1H); LRMS calcd 217.23, found [M−H] 216.1.

Workup

  1. customseparated
  2. washThe separated organic phase is washed with water twice
  3. concentrationThe filtrate is concentrated directly
  4. customMost of the DMF is removed by high vacuum
  5. customto give a brown wet solid
  6. stirringstirred
  7. filtrationfiltered
  8. customto give a brown solid which
  9. customis dried in air overnight

Sources & evidence

ORD record
ord-884a00b6d574413e9214af7d7a00d295
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

Loading…