2,2,2'-Trimethylpropionanilide → HCID 15085941、化合物

HRID 257100

反応式

HRID 257100 の反応式
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:4].C([Li])CCC.[CH3:20][N:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]>O1CCCC1>[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:22]([NH:21][CH3:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:4]

参加物

5

反応物 3

HCID 27340052,2,2'-TrimethylpropionanilideHCID 1245189018100-53-3HCID 178418339Butyllithium

生成物 1

HCID 15085941HCID 15085941、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A chilled solution (-4° C.) of 126 g of 2,2-dimethyl-N-[(2-methyl)phenyl]propanamide in 900 ml of tetrahydrofuran was treated dropwise over 1.5 hr with n-butyl lithium (500 ml of a 2.5M solution in hexanes). After the addition was complete, the resulting solution was stirred for 1 hr, with cooling, and was then treated over 0.5 hr with a solution of 91.77 g of 2-methylbenzaldehyde methyl imine. The reaction mixture was quenched by rapid addition of water. After concentration the residue was extracted with dichloromethane. The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated. A 50 g portion of the residue (213 g) was acidified with 10% hydrochloric acid and partitioned with toluene. The aqueous layer was basified with a 50% sodium hydroxide solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated. Upon standing under nitrogen overnight in a refrigerator a solid formed, which was triturated with hexane to give 2,2-dimethyl-N-[2 -[2-methylamino-2-(2-methylphenyl)ethyl]phenyl]propanamide, mp 77°-79° C.

後処理

  1. additionAfter the addition
  2. temperaturewith cooling
  3. customThe reaction mixture was quenched by rapid addition of water
  4. concentrationAfter concentration the residue
  5. extractionwas extracted with dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompartitioned with toluene
  11. extractionextracted with dichloromethane
  12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  13. concentrationconcentrated
  14. waitUpon standing under nitrogen overnight in a refrigerator
  15. customa solid formed
  16. customwhich was triturated with hexane

出典と根拠

ORDレコード
ord-6aac3a45d85e478593865e2ab42e6ed3
出典データセット
uspto-grants-1993_11
特許番号
US05260339

関連ノート

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