Ammonia → HCID 10264843, compound

HRID 1708210Notes

Reaction equation

HRID 1708210 reaction equation
[Li].[NH3:2].[NH2-].[Li+].C[C:6]1[C:14]2[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[C:12]([C:19](O)=[O:20])[S:11][C:10]=2[CH:9]=[C:8]([O:22][CH3:23])[CH:7]=1>O1CCCC1>[CH3:23][O:22][C:8]1[CH:7]=[CH:6][C:14]2[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[C:12]([C:19]([NH2:2])=[O:20])[S:11][C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 24532Lithium amideHCID 3028194LithiumHCID 18961227HCID 18961227, compound

Product 1

HCID 10264843HCID 10264843, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Excess lithium (74 mg, 10 mM) is added portionwise to a -78° C. solution of a catalytic amount of ferric nitrate in 10 mL of liquid ammonia. The dry ice/acetone bath is removed to allow the reaction to warm to reflux. When the gray color of lithium amide remains for 10 minutes, 2 mL of freshly distilled tetrahydrofuran is added slowly followed by a solution of methyl 6-methoxy-3-(-methylethoxy)benzo[b]thiophene-2-carboxylic acid (200 mg, 0.71 mM) in 2 mL of tetrahydrofuran. The ammonia is allowed to evaporate. The reaction solution is diluted with ethyl acetate, washed with aqueous hydrochloric acid, followed by water, then brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crystalline residue is suspended in 1:9 ethyl acetate:hexane, filtered, and dried at 50° C. in vacuo affording 125 mg (66%) of colorless crystals, mp 164°-166° C.

Workup

  1. customThe dry ice/acetone bath is removed
  2. customthe reaction
  3. temperatureto warm to reflux
  4. customto evaporate
  5. additionThe reaction solution is diluted with ethyl acetate
  6. washwashed with aqueous hydrochloric acid
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. filtrationhexane, filtered
  11. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-68f0a3adedd449beac1e83ebc97f5fe3
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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