Dimethyl Sulfoxide → 2-(1-Azetidinyl]ethyl-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione oxalate

HRID 4865

反応式

HRID 4865 の反応式
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[S:17])[C:4]=2[CH:3]=1.[C:18](=[O:21])([O-:20])[O-].[K+].[K+].[NH:24]1[CH2:27][CH2:26][CH2:25]1.CS(C)=[O:30]>O>[C:10]([OH:9])(=[O:30])[C:18]([OH:20])=[O:21].[N:24]1([CH2:14][CH2:13][CH:8]2[CH2:7][N:6]([CH3:16])[C:5](=[S:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:12]=[N:11][C:10]=3[O:9]2)[CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine3 回HCID 11430Potassium CarbonateHCID 137264487-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)thione

生成物 1

HCID 137266202-(1-Azetidinyl]ethyl-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione oxalate収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 4.75 g (0.0164 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 40 ml of dimethyl sulfoxide was added 8.0 g of crushed potassium carbonate and 1.4 g (0.0246 mole) of azetidine. The flask was sealed and stirred at room temperature for 24 hr after which an additional 0.6 g (0.011 mole) of azetidine was added. After 24 hr, another 0.5 (0.009 mole) of azetidine was added and stirring continued at room temperature. After 48 hr, the entire reaction mixture was diluted with 200 ml of water and extracted with 2×100 ml of benzene. The organic extracts were combined, washed with 3×100 ml of water and 1×100 ml saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated by rotary evaporation (65° C., 30 mm Hg). The residue was treated with oxalic acid in isopropyl alcohol to give 5.4 g (82%) of yellow crystals, m.p. 146°-150° C.

後処理

  1. customThe flask was sealed
  2. additionwas added
  3. customcontinued at room temperature
  4. waitAfter 48 hr
  5. customthe entire reaction mixture
  6. extractionextracted with 2×100 ml of benzene
  7. washwashed with 3×100 ml of water and 1×100 ml saturated sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation (65° C., 30 mm Hg)
  11. additionThe residue was treated with oxalic acid in isopropyl alcohol

出典と根拠

ORDレコード
ord-708edbb82c3846ab9c16f701e9c84890
出典データセット
uspto-grants-1988_02
特許番号
US04727152

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