Formic Acid → Ethyl 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetate

HRID 261688

반응식

HRID 261688 반응식
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH3:11][O:12][N:13]=[C:14]([C:20]1[N:21]=[C:22]([NH2:25])[S:23][CH:24]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O>[CH3:11][O:12][N:13]=[C:14]([C:20]1[N:21]=[C:22]([NH:25][CH:1]=[O:3])[S:23][CH:24]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

생성물 1

HCID 53737196Ethyl 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetate수율 81.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture of acetic anhydride (6.1 g) and formic acid (2.8 g) was stirred for 2 hours at 50° C. The resulting mixture was cooled and ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (4.6 g) was added thereto at 15° C. After the mixture was stirred for 3.5 hours at ambient temperature, cooled water (100 ml) was added thereto. The resulting mixture was extracted with ethyl acetate (200 ml). The extract was washed with water and then with a saturated aqueous solution of sodium bicarbonate until the washing was changed to weakly alkaline solution. The extract was further washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was washed with diisopropyl ether, collected by filtration and dried to give ethyl 2-methoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetate (syn isomer) (4.22 g), mp 122° to 124° C. (dec.).

후처리

  1. temperatureThe resulting mixture was cooled
  2. customat 15° C
  3. stirringAfter the mixture was stirred for 3.5 hours at ambient temperature
  4. additionwas added
  5. extractionThe resulting mixture was extracted with ethyl acetate (200 ml)
  6. washThe extract was washed with water
  7. washThe extract was further washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off
  10. washthe residue was washed with diisopropyl ether
  11. filtrationcollected by filtration
  12. customdried

출처 및 근거

ORD 기록
ord-937c68930208408cae827faeab2ccc3a
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166115

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