Ammonium Acetate → HCID 15565856, compound

HRID 902483Notes

Reaction equation

HRID 902483 reaction equation
C([O-])(=[O:3])C.[NH4+].[CH2:6]([O:8][C:9]([C:11]1[C:12]([Cl:21])=[C:13]2[S:20][CH:19]=[CH:18][C:14]2=[N:15][C:16]=1Cl)=[O:10])[CH3:7]>C(O)(=O)C>[CH2:6]([O:8][C:9]([C:11]1[C:16](=[O:3])[NH:15][C:14]2[CH:18]=[CH:19][S:20][C:13]=2[C:12]=1[Cl:21])=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 15565855HCID 15565855, compound

Product 1

HCID 15565856HCID 15565856, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

Ammonium acetate (161 mg, 2.1 mmol) was added to a stirred solution of 5,7-dichloro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (3) (530 mg, 1.9 mmol) in glacial acetic acid at room temperature. The solution was heated at 140° C. for 48 h. The hot solution was poured into ice water. The solids formed were filtered, washed by water, and dried. The crude product was recrystallized by CH2Cl2 to yield 273 mg (60%) of 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester as white solids. MP 206° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, J=7.2 Hz, 3H), 4.29 (q, J=7.2 Hz, 2H), 7.10 (d, J=5.2 Hz, 1H), 8.13 (d, J=5.2 Hz, 1H) ppm; MS m/z=240 amu (M++1).

Workup

  1. customThe solids formed
  2. filtrationwere filtered
  3. washwashed by water
  4. customdried
  5. customThe crude product was recrystallized by CH2Cl2

Sources & evidence

ORD record
ord-8b3a293f112948e5aefdf931d970d52d
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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