Hydrochloric Acid → n-(2,6-Dichloro-4-methoxycarbonylphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide

HRID 322033노트

반응식

HRID 322033 반응식
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:13].ClC1C=NC=C(Cl)C=1NC(C1C=CC(OC)=C2OC(C)=CC=12)=O.[CH3:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([C:51](O)=[O:52])=[C:43]2[C:47]=1[O:46][C:45]([CH:48]([CH3:50])[CH3:49])=[CH:44]2.S(Cl)(Cl)=O.Cl>O1CCCC1.C1(C)C=CC=CC=1.C(N(CC)CC)C>[Cl:13][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[C:11]([Cl:12])[C:2]=1[NH:1][C:51]([C:42]1[CH:41]=[CH:40][C:39]([O:38][CH3:37])=[C:47]2[O:46][C:45]([CH:48]([CH3:50])[CH3:49])=[CH:44][C:43]=12)=[O:52]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 604808Methyl 4-amino-3,5-dichlorobenzoateHCID 220095277-Methoxy-2-(1-methylethyl)benzofuran-4-carboxylic acidHCID 22009540n-(3,5-Dichloropyrid-4-yl)-7-methoxy-2-methylbenzofuran-4-carboxamide

생성물 1

HCID 22009528n-(2,6-Dichloro-4-methoxycarbonylphenyl)-7-methoxy-2-(1-methylethyl)benzofuran-4-carboxamide

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

2.0 g of triethylamine were added to a solution of 4.4 g of methyl 4-amino-3,5-dichlorobenzoate in 50 ml of tetrahydrofuran and the mixture was stirred (solution 1). In parallel to this, 4.7 g of 7-methoxy-2-(1-methylethyl)benzofuran-4-carboxylic acid were stirred at 80° C. for 3 h with 10.0 ml of thionyl chloride in 40 ml of toluene and the mixture was then evaporated in vacuo. About 20 ml of toluene were added to the residue and the solution was evaporated again in vacuo. The residue was then taken up in 50 ml of tetrahydrofuran and this solution was added dropwise at RT to the prepared solution 1. After reaction was complete, the mixture was stirred into about 200 ml of ice water, treated with 30 ml of 2 N hydrochloric acid and extracted with ethyl acetate. This extract was dried over calcined sodium sulfate and evaporated in vacuo. The residue was crystallized from toluene: m.p. 175° C.

후처리

  1. customthe mixture was then evaporated in vacuo
  2. additionAbout 20 ml of toluene were added to the residue
  3. customthe solution was evaporated again in vacuo
  4. additionthis solution was added dropwise at RT to the prepared solution 1
  5. customAfter reaction
  6. extractionextracted with ethyl acetate
  7. customThis extract was dried
  8. customevaporated in vacuo
  9. customThe residue was crystallized from toluene

출처 및 근거

ORD 기록
ord-a8e10ba7c2fb4d1084288448bf8dd747
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211203B1

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