3-Thiophenacetic acid → Ethyl acetate methanol ammonia

HRID 1014935Notes

Reaction equation

HRID 1014935 reaction equation
[O:1]1C2C=CC=CC=2[NH:4]C[CH2:2]1.S1C=CC([CH2:16][C:17]([OH:19])=[O:18])=C1.[CH3:20][CH2:21]N(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C=O)C>[NH3:4].[CH3:2][OH:1].[CH3:20][CH2:21][O:19][C:17]([CH3:16])=[O:18]

Participants

8

Reactant 5

HCID 234043-Thiophenacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 21873639Ethyl acetate methanol ammoniaYield 0%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 3,4-dihydro-2H-1,4-benzoxazine (0.52 g, 3.8 mmol) and thiophene-3-acetic acid (0.82 g, 5.7 mmol) in 1:1 CH2Cl2:DMF (20 mL) was treated with DIPEA (2.6 ml, 15 mmol), HOBt (1.29 g, 9.5 mmol), and EDCl (1.83 g, 9.5 mmol) and stirred at 70° C. overnight. The reaction was then diluted with CH2Cl2, washed with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated. Chromatography (0-10% 1 N NH3-MeOH/EtOAc) provided 2A as a red solid (0.54 g, 55%)

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-29b148bfef7e4fe4b93d457f3f568aa7
Source dataset
uspto-grants-2011_07
Patent number
US07985748B2

Reaction notes

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