Sodium hydride → HCID 59180379, compound

HRID 1925691Notes

Reaction equation

HRID 1925691 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([O:15][CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]([O:25][CH3:26])=[O:24].[H-].[Na+]>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:17][C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])(=[O:13])=[O:12])=[C:7]([O:15][CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 591803954-(1,1-Dimethylethyl)-2-methoxybenzenesulfonyl chloride

Product 1

HCID 59180379HCID 59180379, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 31 (8.45 g; 32.16 mmol) and methyl 3-aminothiophene-2-carboxylate (5.60 g; 35.38 mmol) in tetrahydrofuran (160 mL) at room temperature was added sodium hydride (1.5 g; 38.59 mmol; 60% mineral oil). The reaction mixture was stirred at room temperature under nitrogen for 16 hours (an additional equivalent of sodium hydride was found to be necessary to drive reaction to an acceptable level of completion) and then quenched with water and aqueous hydrochloric acid (2N) and extracted with ethyl acetate. The combined organic phases were successively washed with water and aqueous saturated sodium chloride, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting crude residue was taken up in ethyl acetate. The resulting precipitate was filtered and triturated from diethyl ether to yield the title compound as a light brown solid (3.58 g).

Workup

  1. customreaction to an acceptable level of completion) and
  2. customthen quenched with water and aqueous hydrochloric acid (2N)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were successively washed with water and aqueous saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. filtrationThe resulting precipitate was filtered
  9. customtriturated from diethyl ether

Sources & evidence

ORD record
ord-a99403637d9346b382362633f1ec40a4
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

Loading…