Thionyl Chloride → 4,4-Dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline

HRID 840346

反応式

HRID 840346 の反応式
S(Cl)(Cl)=O.[O:5]=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([NH:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=O)=[CH:12][CH:13]=2)[CH2:8][O:7]1>C1(C)C=CC=CC=1>[CH3:21][C:18]1([CH3:22])[CH2:19][O:20][C:15]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[C:6](=[O:5])[O:7][CH2:8]3)=[N:17]1

参加物

4

反応物 2

HCID 24386Thionyl Chloride2 回HCID 111960052-[[(1-Oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl]amino]-2-methyl-1-propanol

生成物 1

HCID 113221954,4-Dimethyl-2-(1-oxo-1,3-dihydroisobenzofuran-5-yl)oxazoline

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
29 °C

実験手順

To stirred thionyl chloride (800 ml), at 0° C., 2-[[(1-oxo-1,3-dihydroisobenzofuran-5-yl)carbonyl]amino]-2-methyl-1-propanol (560 g, 2.25 mol) is added portionwise while maintaining the temperature below 10° C. The temperature is allowed to rise, and then the mixture is heated between 28-30° C. for 5 hours. The thionyl chloride is destined off under reduce pressure at 60° C. The residue is taken up in toluene (2×700 ml) and concentrated under reduce pressure at 60° C. The solid is filtered off, washed with toluene (2×100 ml) and dried at in vacuo. The product is suspended in deionized water (3000 ml). The suspension is cooled and pH is adjusted to basic pH by addition of 28% aqueous ammonia (1000 ml). The product is filtered off, washed with deionized water, and dried at 50° C. in vacuo. Yield: 407 g (78%) having m.p.=109-111° C. and purity (HPLC, peak area)≧95%.

後処理

  1. temperaturewhile maintaining the temperature below 10° C
  2. customat 60° C
  3. concentrationconcentrated
  4. customat 60° C
  5. filtrationThe solid is filtered off
  6. washwashed with toluene (2×100 ml)
  7. customdried at in vacuo
  8. temperatureThe suspension is cooled
  9. additionpH is adjusted to basic pH by addition of 28% aqueous ammonia (1000 ml)
  10. filtrationThe product is filtered off
  11. washwashed with deionized water
  12. customdried at 50° C. in vacuo

出典と根拠

ORDレコード
ord-b62fd3f6830f43d9b827b28a86eb263d
出典データセット
uspto-grants-2002_04
特許番号
US06365747B1

関連ノート

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