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

HRID 1290623ノート

反応式

HRID 1290623 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2b2b3c8010b34327bf47eae8d0a97f75
出典データセット
uspto-grants-1998_05
特許番号
US05753595

反応ノート

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