Chloride → 2-[[(1-Oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl]amino]-2-methyl-1-propanol

HRID 1072764

反応式

HRID 1072764 の反応式
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)([OH:3])=O.S(Cl)(Cl)=O.[NH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21].[Cl-]>O1CCCC1.C1(C)C=CC=CC=1.CN(C)C=O>[O:10]=[C:9]1[C:11]2[C:6](=[CH:5][C:4]([C:1]([NH:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[O:3])=[CH:13][CH:12]=2)[CH2:7][O:8]1

参加物

8

反応物 4

HCID 312ChlorideHCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl Chloride2 回HCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

生成物 1

HCID 111960052-[[(1-Oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl]amino]-2-methyl-1-propanol

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

5-carboxyphthalide (267 g, 1.5 mol) is added to thionyl chloride (950 mL) and then N,N-dimethylformamide (12 mL) is added dropwise. The mixture is heated at reflux for 1 hour and the thionyl chloride is destined off under reduced pressure followed by successive evaporations with toluene (2×50 mL) to give a solid residue. The crude acid chloride is then taken up with 1000 mL of tetrahydrofuran. To a solution of 2-amino-2-methyl-1-propanol (400.5 g, 4.5 mol) in tetrahydrofuran (500 mL), cooled to +5° C. chloride solution is added dropwise whilst maintaining the temperature between +5→+10° C. After the addition is completed, the cooling is removed and the mixture is stirred overnight at ambient temperature. Then the mixture is poured into deionized water (2000 mL) and the organic solvent is removed under reduced pressure at 50° C. After cooling and stirring for 2 hours, the solid product is filtered off and washed with deionized water (2×100 mL). The obtained product is dried at 70° C. for 36 hours under reduced pressure. Yield: 285.3 g (76%) of an off-white product having a purity (HPLC, peak area)=90%. 1H NMR (DMSO d-6, 500 MHz): 1.18 (3H, s), 1.32 (3H, s), 3.55 (2H, s), 5.45 (2H, s), 7.88-7.98 (3H, m), 8.07 (1H, s).

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 hour
  3. customto give a solid residue
  4. additionis added dropwise
  5. temperaturewhilst maintaining the temperature between +5→+10° C
  6. additionAfter the addition
  7. customthe cooling is removed
  8. additionThen the mixture is poured into deionized water (2000 mL)
  9. customthe organic solvent is removed under reduced pressure at 50° C
  10. temperatureAfter cooling
  11. stirringstirring for 2 hours
  12. filtrationthe solid product is filtered off
  13. washwashed with deionized water (2×100 mL)
  14. customThe obtained product is dried at 70° C. for 36 hours under reduced pressure

出典と根拠

ORDレコード
ord-5c991c8efff04fe8b5c12398f3814bd6
出典データセット
uspto-grants-2005_06
特許番号
US06911548B2

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