Dicyclohexylcarbodiimide → HCID 54547844、化合物

HRID 582286ノート

反応式

HRID 582286 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2C(O)=O)[CH:6]=[CH:7][CH:8]=1.[OH:19]N1C2C=CC=CC=2N=N1.N1CCCC1.C1(N=[C:41]=[N:42][CH:43]2CC[CH2:46][CH2:45][CH2:44]2)CCCCC1>C1COCC1.CC#N.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[CH:15][C:16]([C:41]([N:42]3[CH2:43][CH2:44][CH2:45][CH2:46]3)=[O:19])=[CH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 119702Anthranilic acid, N-(3-methoxyphenyl)-

生成物 1

HCID 54547844HCID 54547844、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22177404Acetonitrile tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2 g (8.2 mmol) of 4-[N-(3-methoxyphenyl)aminobenzoic acid, 2.2 g (16.4 mmol) of N-hydroxybenzotriazole and 1 ml (12.3 mmol) of pyrrolidine were dissolved in 40 ml of a 7:3 mixture of THF/CH3CN, under a nitrogen atmosphere. The solution was cooled to 0° C. and 3.4 g (16.4 mmol) of dicyclohexylcarbodiimide dissolved in 20 ml of CH2Cl2 were added. The reaction mixture was allowed to warm to room temperature during 1 h., stirred an additional hour, then the precipitate was filtered off and the solvent was removed in vacuo. The residue was taken up with water and extracted with AcOEt, the organic layer was dried over Na2SO4 and the solvent removed in vacuo. The resulting crude mixture was purified by flash chromatography (AcOEt), yielding 2.4 g of the title compound.

後処理

  1. additionwere added
  2. temperatureto warm to room temperature during 1 h.
  3. filtrationthe precipitate was filtered off
  4. customthe solvent was removed in vacuo
  5. extractionextracted with AcOEt
  6. dry with materialthe organic layer was dried over Na2SO4
  7. customthe solvent removed in vacuo
  8. customThe resulting crude mixture was purified by flash chromatography (AcOEt)

出典と根拠

ORDレコード
ord-754f0d4c459c4e6083767e74408182d4
出典データセット
uspto-grants-1999_07
特許番号
US05922887

反応ノート

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