3-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehyde → HCID 68440387, compound

HRID 1435866Notes

Reaction equation

HRID 1435866 reaction equation
[Br-].C1([C:8]([PH3+])([C:15]2C=CC=CC=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)C=CC=CC=1.[Li]CCCC.[O:27]=[C:28]1[NH:33]C2C=C(C=O)C=CC=2[S:30][CH2:29]1>C1COCC1>[CH:8]([C:9]1[CH:10]=[CH:11][C:12]2[S:30][CH2:29][C:28](=[O:27])[NH:33][C:13]=2[CH:14]=1)=[CH2:15]

Participants

5

Reactant 3

HCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 68440387HCID 68440387, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of triphenylmethylphosphonium bromide (20.0 mmole) in dry THF (40 mL) at RT was added 2.5 M n-BuLi (7.5 mL, 3.0 mmole). After 3 h, 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxaldehyde (1.93 g, 10.0 mmole) was added and the reaction contents were stirred at RT overnight. The reaction solution was filtered and the filtrate concentrated, dissolved in EtOAc and washed with 1 M HCl (20 mL). The organic solution was dried (Na2SO4) and concentrated under vacuum. Purification on silica (EtOAc/hexanes, 1:4) afforded the title compound (1.20 g, 63%) as light yellow solid: LC-MS (ES): m/e 192 (M+H)+.

Workup

  1. customthe reaction contents
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate concentrated
  4. dissolutiondissolved in EtOAc
  5. washwashed with 1 M HCl (20 mL)
  6. dry with materialThe organic solution was dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customPurification on silica (EtOAc/hexanes, 1:4)

Sources & evidence

ORD record
ord-897346b7488e4abd8cc3ceedb9093924
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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