تفاعل #55883

ord-5a19c020631c4af9a138822f925c795b

معادلة التفاعل

O=C(O)Cc1ccc(OCc2ccccc2)c(Cl)c1
3-chloro-4-benzyloxyphenylacetic acid
[Cl-]
chloride
O=S(Cl)Cl
thionyl chloride
CN(C)CCO
dimethylaminoethanol
[Cl-]
chloride
CN(C)CCOC(=O)Cc1ccc(OCc2ccccc2)c(Cl)c1.Cl
β-dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride
المردود 131.1%

المذيبات

ظروف التفاعل

درجة الحرارة
5°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىso yielding a precipitate which
  2. 2
    ترشيحwas filtered
  3. 3
    غسيلwashed with benzene
  4. 4
    أخرىTwo crystallizations from ethylacetate-isopropyl alcohol (1:1)

الإجراء التجريبي

6.15 grams of 3-chloro-4-benzyloxyphenylacetic acid was converted into the corresponding chloride by treatment with 15 ml of thionyl chloride in 50 ml of benzene. A solution comprising 1.85 grams of dimethylaminoethanol in 10 ml of benzene was slowly added at 20° C. to the chloride solution. The mixture was then permitted to stand for 2 hours at that temperature and then cooled to 5° C., so yielding a precipitate which was filtered and washed with benzene. Two crystallizations from ethylacetate-isopropyl alcohol (1:1) yielded 5.6 grams (68.4%) of β-dimethylaminoethyl 3-chloro-4-benzyloxyphenylacetate hydrochloride, m.p. 138°-140° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04221919uspto-grants-1980_09