Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1493459ノート

反応式

HRID 1493459 の反応式
C(N(CC(O)=O)CCN(CC(O)=O)CC(O)=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=[O:9].ON1C(=O)CCC1=O.[CH:43]1([N:49]=[C:50]=[N:51][CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>CS(C)=O>[CH:52]1([NH:51][C:50](=[O:9])[NH:49][CH:43]2[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]2)[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 70088Triethylenetetraminehexaacetic acidHCID 80170N-Hydroxysuccinimide

生成物 1

HCID 4277N,N'-Dicyclohexylurea

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution consisting of 0.7 g (1.3 mmol) N,N'-(2-aminoethyl) trans-1,2-diaminocyclohexane-N,N',N",N'",N'"hexaacetic acid in 50 ml dimethylsulfoxide was added 0.9 g (7.8 mmol) N-hydroxysuccinimide and 0.8 g (3.9 mmol) dicyclohexylcarbodiimide. This was stirred at room temperature for 48 hr., during which the white fluffy solid of dicyclohexyl urea formed. This solid was removed by filtration and the filtrate was concentrated to a thick oil under reduced pressure. A solid precipitated from the oil upon the addition of acetonitrile. This solid was collected, washed with cold acetonitrile and dried under vacuum to give 0.54 g of a light brown solid. NMR showed an average of 2 NHS esters so the yield is 56%. No further purification of the solid was attempted; mp 125°-140° C.

出典と根拠

ORDレコード
ord-2afdaad5e4ef4ac9be98e60a4c91f1a9
出典データセット
uspto-grants-1991_06
特許番号
US05021571

反応ノート

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