Hydrochloric Acid → Butyl 2-(4-chloro-2-nitrobenzoyl)-2-cyanoacetate

HRID 2231158노트

반응식

HRID 2231158 반응식
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:5])#[N:2].C(N(CC)CC)C.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=1.[OH-].[Na+].Cl>C1COCC1.C(Cl)Cl>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:5])=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 79571Butyl cyanoacetateHCID 108677844-Chloro-2-nitrobenzoyl chloride

생성물 1

HCID 21286077Butyl 2-(4-chloro-2-nitrobenzoyl)-2-cyanoacetate수율 63.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Butyl cyanoacetate (6.35 g; 0.05 mol) and triethylamine (20.9 ml; 0.15 mol) were dissolved in dry THF (100 ml) under dry nitrogen, and 4-chloro-2-nitrobenzoyl chloride (11.0 g; 0.05 mol) in dry THF (100 ml) added dropwise over 45 min. The mixture was stirred at room temperature under dry nitrogen for 18 hours, during which time a precipitate was formed. The solution was filtered and evaporated, giving a residue which was treated with 2M sodium hydroxide solution (200 ml) and CH2Cl2 (100 ml). This formed three layers. The middle layer was treated with 2M hydrochloric acid (50 ml) and extracted into CH2Cl2 (3×50 ml). The extracts were combined, dried (Na2SO4), filtered and evaporated, giving butyl 2-(4-chloro-2-nitrobenzoyl)-2-cyanoacetate (10.27 g; 63%) as a yellow solid, m.p. 56°-58° C., (Found, C: 52.01; H: 4.05; N: 8.70; Cl: 10.97. C14H13ClN2O5 requires C: 51.77; H: 4.01; N: 8.63; Cl: 10.94%), d (CDCl3 ; 60 MHz) 0.8-2.1 (7H, m), 4.4 (2H, t, J=6 Hz), 7.65 (2H, m), 8.15 (1H, d, J=2 Hz) and 13.0 (1H, br, s), vmax (nujol) 2230, 1660, 1610, 1590 and 1540.

후처리

  1. customwas formed
  2. filtrationThe solution was filtered
  3. customevaporated
  4. customgiving a residue which
  5. customThis formed three layers
  6. extractionextracted into CH2Cl2 (3×50 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-db913d360702497cb90640652b1d35fa
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04781750

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