1,3-Di-Boc-2-methylisothiourea → HCID 86646935、化合物

HRID 1929340ノート

反応式

HRID 1929340 の反応式
CS/[C:3](/[NH:12][C:13](=O)OC(C)(C)C)=[N:4]\[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]([NH2:32])C(N)=[CH:29][CH:30]=1>CO.C(O)(=O)C>[Cl:20][C:21]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:22]=1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:13]2[N:12]=[C:3]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[NH:32][C:27]=2[CH:26]=1

参加物

5

反応物 2

HCID 63760081,3-Di-Boc-2-methylisothioureaHCID 68511467HCID 68511467、化合物

生成物 1

HCID 86646935HCID 86646935、化合物収率 67.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

add 615 mg of bis(1,1-dimethylethyl) [(Z)-(methylsulphanyl)methylylidene]biscarbamate to a solution of 600 mg of 4-[(2,6-dichlorobenzyl)oxy]benzene-1,2-diamine in a mixture of 30 cm3 of methanol and 127 mg of pure acetic acid. The mixture is refluxed for about 3 hours then concentrated under reduced pressure (0.2 kPa). The residue is taken up in 20 cm3 of a saturated aqueous solution of potassium carbonate and the mixture is extracted three times with 100 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulphate, then filtered and evaporated under reduced pressure. After purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we obtain 586 mg of 1,1-dimethylethyl {6-[(2,6-dichlorobenzyl)oxy]-1H-benzimidazol-2-yl}carbamate in the form of an orange resin, which has the following characteristics:

後処理

  1. temperatureThe mixture is refluxed for about 3 hours
  2. concentrationthen concentrated under reduced pressure (0.2 kPa)
  3. extractionthe mixture is extracted three times with 100 cm3 of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customAfter purification of the residue by silica-column flash chromatography [eluent: dichloromethane/methanol (98/2 by volume)], we

出典と根拠

ORDレコード
ord-32f46420833d4d768ba7cd58eb7cf23b
出典データセット
uspto-grants-2012_05
特許番号
US08188078B2

反応ノート

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