Acetyl chloride → Methyl 4-(2-aminoethoxy)benzoate hydrochloride

HRID 29711

反応式

HRID 29711 の反応式
C(OC(=O)[NH:7][CH2:8][CH2:9]O)(C)(C)C.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C([Cl:59])(=O)C>O1CCCC1>[ClH:59].[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:9][CH2:8][NH2:7])=[CH:17][CH:16]=1

参加物

7

反応物 5

HCID 6367Acetyl chlorideHCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

生成物 1

HCID 50988568Methyl 4-(2-aminoethoxy)benzoate hydrochloride収率 93.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

(2-Hydroxyethyl)carbamic acid tert-butyl ester (152.0 g, 0.942 mol) and 4-hydroxybenzoic acid methyl ester (174.0 g, 1.12 mol) were dissolved in tetrahydrofuran (2000 ml) and cooled to 0-5° C. Triphenylphosphine (292.8 g 1.116 mol) was added to the cooled mixture. A solution of diisopropyl azodicarboxylate (246.0 g, 1.218 mol) in tetrahydrofuran (400 ml) was added dropwise over a period of one to two hours keeping the reaction temperature below 10° C. After addition, the reaction was allowed to warm slowly to ambient temperature and stirred overnight. After completion of reaction, solvent was distilled under reduced pressure and the resulting oil was dissolved in ethanol (500 ml) and ethyl acetate (2000 ml). Acetyl Chloride (222.0 g, 2.826 mol) was added drop wise over fifteen minutes with the temperature allowed to rise to 40° C. The resulting suspension was stirred at 40° C. until completion of reaction. After completion of reaction, the resulting crystals were filtered on a coarse frit and washed with ethyl Acetate (300 mL). The material is dried in vacuo to give of 4-(2-aminoethoxy)benzoic acid methyl ester hydrochloride (204.1 g) as a white crystalline solid.

後処理

  1. customthe reaction temperature below 10° C
  2. additionAfter addition
  3. temperatureto warm slowly to ambient temperature
  4. customAfter completion of reaction, solvent
  5. distillationwas distilled under reduced pressure
  6. dissolutionthe resulting oil was dissolved in ethanol (500 ml)
  7. customto rise to 40° C
  8. stirringThe resulting suspension was stirred at 40° C. until completion of reaction
  9. customAfter completion of reaction
  10. filtrationthe resulting crystals were filtered on a coarse frit
  11. washwashed with ethyl Acetate (300 mL)
  12. customThe material is dried in vacuo

出典と根拠

ORDレコード
ord-1e38f5e010734ba593a554c9bb24cb2d
出典データセット
uspto-grants-2008_09
特許番号
US07420089B2

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