Aluminium lithium hydride → HCID 22593772, compound

HRID 1920980Notes

Reaction equation

HRID 1920980 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:9]([CH3:10])[C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:10][N:9]1[C:5]([CH2:3][NH:2][CH3:1])=[CH:6][C:7]2[CH:13]=[CH:12][S:11][C:8]1=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22593776HCID 22593776, compound

Product 1

HCID 22593772HCID 22593772, compoundYield 114.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N,6-dimethyl-6H-thieno[2,3-b]pyrrole-5-carboxamide (134 mg, 0.69 mmole) in dry THF (5 mL) was added a solution of LiAlH4 in THF (1.0 M, 1.38 mL, 1.38 mmole) slowly at RT. After gas evolution had ceased the mixture was heated to a gentle reflux. After 2 hr the mixture was cooled to RT and quenched by dropwise addition of 2M NaOH until a white solid had formed. The mixture was dried (MgSO4, filtered, and concentrated to give the title compound as a brown oil (142 mg, 100%) which was sufficiently pure for use in the next step: 1H NMR (400 MHz, CDCl3) δ 6.95 (d, J=5.2 Hz, 1H), 6.78 (d, J=5.2 Hz, 1H), 6.27 (s, 1H), 3.78 (s, 2H), 3.72 (s, 3H), 2.47 (s, 3H).

Workup

  1. temperaturewas heated to a gentle reflux
  2. customquenched by dropwise addition of 2M NaOH until a white solid
  3. customhad formed
  4. dry with materialThe mixture was dried (MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45964079f2944b51b4529bc55488d7e9
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

Loading…