tert-Butanol → Ethyl 6-(tert-butoxycarbonylamino)-3-pyridazine carboxylate

HRID 1455988

반응식

HRID 1455988 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[N-:13]=[C:14]=[O:15].[K+].[C:17]([OH:21])([CH3:20])([CH3:19])[CH3:18].COCCOCCOC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]([O:21][C:14]([NH:13][C:2]1[N:7]=[N:6][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8150DiglymeHCID 10352425Ethyl 6-chloropyridazine-3-carboxylateHCID 11051572Potassio isocyanate

생성물 1

HCID 22105617Ethyl 6-(tert-butoxycarbonylamino)-3-pyridazine carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of ethyl 6-chloro-3-pyridazine carboxylate (6.5 g) [British patent number 856, 409], potassium isocyanate (3.5 g), tert-butanol (6.0 ml), tetrakis(triphenylphosphine)palladium (400 mg) and diglyme (6 ml) in DMF (50 ml) was heated at reflux for 2 hours, cooled and partitioned between diethyl ether and water. The organic layer was dried (MgSO4), filtered through silica gel and evaporated. The resulting solid was purified by crystallisation from iso-hexane to give ethyl 6-(tert-butoxycarbonylamino)-3-pyridazine carboxylate (2.4 g), mp 87°-88° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. custompartitioned between diethyl ether and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered through silica gel
  7. customevaporated
  8. customThe resulting solid was purified by crystallisation from iso-hexane

출처 및 근거

ORD 기록
ord-cb5abc9447dc4bcd929602a6aed871a5
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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