Thiourea → Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide

HRID 261686노트

반응식

HRID 261686 반응식
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12][Br:13])=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[BrH:13].[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:14]=[C:15]([NH2:17])[S:16][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

4

반응물 2

HCID 2723790ThioureaHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

생성물 1

HCID 73668749Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of ethyl 2-methoxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (17.4 g.) and thiourea (5.4 g.) in ethanol (100 ml.) was refluxed for 4 hours. The reaction mixture was allowed to stand and cooled in refrigerator to precipitate crystals. The crystals were collected by filtration, washed with ethanol and dried to give ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate hydrobromide (anti isomer) (9.5 g.). The filtrate and the washings were put together and concentrated under reduced pressure. Water (100 ml.) was added to the residue and the mixture was washed with ether. The aqueous layer was alkalized with a 28% aqueous solution of ammonia and extracted with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give crystalline substance of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (5.2 g.).

후처리

  1. temperaturewas refluxed for 4 hours
  2. temperaturecooled in refrigerator
  3. customto precipitate crystals
  4. filtrationThe crystals were collected by filtration
  5. washwashed with ethanol
  6. customdried

출처 및 근거

ORD 기록
ord-793a1f17eedf476a8a6ea30323bc8ea5
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166115

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