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

HRID 1455988

反応式

HRID 1455988 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cb5abc9447dc4bcd929602a6aed871a5
出典データセット
uspto-grants-1998_12
特許番号
US05843942

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