Hydrochloric Acid → ethyl N-(2-t-butyl-4-chloro-6-fluorobenzoxazol-7-yl)carbamate

HRID 1290623

반응식

HRID 1290623 반응식
[C:1]([C:5]1[O:6][C:7]2[C:13]([NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[C:12]([F:20])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:22]N(Cl)C(OCC)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)(=O)C>[C:1]([C:5]1[O:6][C:7]2[C:13]([NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[C:12]([F:20])[CH:11]=[C:10]([Cl:22])[C:8]=2[N:9]=1)([CH3:2])([CH3:4])[CH3:3]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 26195N,N-DichlorourethanHCID 516892Sodium BicarbonateHCID 18916412ethyl N-(2-t-butyl-6-fluorobenzoxazol-7-yl)carbamate

생성물 1

HCID 18916422ethyl N-(2-t-butyl-4-chloro-6-fluorobenzoxazol-7-yl)carbamate수율 69.3%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

Under a nitrogen atmosphere, a solution of 3.1 grams (11.0 mmole) of ethyl N-(2-t-butyl-6-fluorobenzoxazol-7-yl)carbamate, 35 mL of acetic acid, and 0.2 mL (2.4 mmole) of concentrated hydrochloric acid was stirred and cooled in an ice bath. During five minutes 2.2 grams (14 mmole) of N,N-dichlorourethane was added via syringe. Upon completion of the addition the reaction mixture was stirred for 4 hours, then analyzed by TLC, which indicated the reaction was complete. The reaction mixture was poured into 100 mL of water, and 15 mL of aqueous saturated sodium bicarbonate solution was carefully added. The reaction mixture was then extracted with two 75 mL portions of diethyl ether, and the combined extracts were concentrated under reduced pressure, yielding a residual oil. The oil was subjected to column chromatography on silica gel with 8:1 hexane:ethyl acetate as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.4 grams of ethyl N-(2-t-butyl-4-chloro-6-fluorobenzoxazol-7-yl)carbamate, m.p. 127°-129° C. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperaturecooled in an ice bath
  2. additionUpon completion of the addition the reaction mixture
  3. additionwas carefully added
  4. extractionThe reaction mixture was then extracted with two 75 mL portions of diethyl ether
  5. concentrationthe combined extracts were concentrated under reduced pressure
  6. customyielding a residual oil
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2b2b3c8010b34327bf47eae8d0a97f75
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753595

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