Hydrochloric Acid → Ethyl 2-((6-amino-2,3-dichlorobenzyl)amino)acetate

HRID 614901ノート

反応式

HRID 614901 の反応式
[NH2:1][C:2]1[C:7]([CH2:8]O)=[C:6]([Cl:10])[C:5]([Cl:11])=[CH:4][CH:3]=1.Cl.S(Cl)(Cl)=O.Cl.[CH2:18]([O:20][C:21](=[O:24])[CH2:22][NH2:23])[CH3:19].C(N(CC)CC)C>C(Cl)Cl.C1C=CC=CC=1>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][NH:23][CH2:8][C:7]1[C:2]([NH2:1])=[CH:3][CH:4]=[C:5]([Cl:11])[C:6]=1[Cl:10])[CH3:19]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 14998901(6-Amino-2,3-dichlorophenyl)methanol

生成物 1

HCID 9814186Ethyl 2-((6-amino-2,3-dichlorobenzyl)amino)acetate

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 6-amino-2,3-dichlorobenzyl alcohol (10.0 g., 0.0521 mol) in 250 ml. of boiling benzene was treated with a slow-stream of dry hydrogen chloride for 0.5 hour. The finely divided suspension was cooled slightly, thionyl chloride (12.4 g, 0.104 mol) was added in one portion, and reflux was continued for 2.5 hours. The solution was evaporated in vacuo to remove excess thionyl chloride and hydrogen chloride, and the residue was redissolved in 250 ml. benzene. This solution was added over 1 hour to a reluxing mixture of glycine ethyl ester hydrochloride (29.1 g, 0.208 mol) and triethylamine (31.6 g, 0.313 mol) in 600 ml. CH2Cl2. Reflux was continued for 1 hour, the mixture was allowed to stand overnight and was then extracted with 1N HCl. The extract was washed with CH2Cl2 and ether, made slightly alkaline with concentrated NH4OH and extracted with ether. After drying (K2CO3) and evaporation there remained 8.3 g (58%) of the title product as a light yellow oil which crystallized. The analytical sample was obtained from Skellysolve B as white needles, mp. 60°-61° C.

後処理

  1. temperatureThe finely divided suspension was cooled slightly
  2. temperaturereflux
  3. customThe solution was evaporated in vacuo
  4. customto remove excess thionyl chloride and hydrogen chloride
  5. dissolutionthe residue was redissolved in 250 ml
  6. temperatureReflux
  7. waitwas continued for 1 hour
  8. waitto stand overnight
  9. extractionwas then extracted with 1N HCl
  10. washThe extract was washed with CH2Cl2 and ether
  11. extractionextracted with ether
  12. customAfter drying
  13. custom(K2CO3) and evaporation there remained 8.3 g (58%) of the title product as a light yellow oil which
  14. customcrystallized
  15. customThe analytical sample was obtained from Skellysolve B as white needles, mp. 60°-61° C.

出典と根拠

ORDレコード
ord-6e433e8af9b3482db8a47eed61192c77
出典データセット
uspto-grants-1979_03
特許番号
US04146718

反応ノート

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