Methylamine → HCID 21426078, compound

HRID 258583Notes

Reaction equation

HRID 258583 reaction equation
Br[CH2:2][CH2:3][C:4]1([CH3:19])[C:12]2[S:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:9][C:8]=2[CH2:7][CH2:6][O:5]1.[CH3:20][NH2:21]>O1CCCC1>[CH3:20][NH:21][CH2:2][CH2:3][C:4]1([CH3:19])[C:12]2[S:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:9][C:8]=2[CH2:7][CH2:6][O:5]1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 12429026HCID 12429026, compound

Product 1

HCID 21426078HCID 21426078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-bromoethyl)-6,7-dihydro-4-methyl-2-phenyl-4H-pyrano[ 4,3-d]thiazole (3.14 g, 9.28 mmoles, described above) in dry tetrahydrofuran (50 ml), methylamine gas is slowly added during one hr. After standing overnight additional methylamine gas is introduced and the solution is allowed to stand for 24 hr. After evaporation under reduced pressure the residue is taken up in aqueous sodium bicarbonate solution and extracted with chloroform. The organic extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is dissolved in acetone-ether and the crystalline precipitate is removed by filtration. The filtrate is evaporated under reduced pressure to give the title compound, nmr (CDCl3) δ 1.57 (s, 3H), 2.07 (t, J= 5Hz), 2.44 (s, 3H), 2.60 (m, 2H), 2.94 (t, J= 5.5 Hz), 4.10 (t, J= 5.5 Hz), 7.5-8.0 (m, 5H), identical to the amine described in Example 31.

Workup

  1. waitto stand for 24 hr
  2. customAfter evaporation under reduced pressure the residue
  3. extractionextracted with chloroform
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. dissolutionThe residue is dissolved in acetone-ether
  9. customthe crystalline precipitate is removed by filtration
  10. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-006d0bb4944c422fbc9e9120dd293a04
Source dataset
uspto-grants-1977_07
Patent number
US04033977

Reaction notes

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