Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1493459노트

반응식

HRID 1493459 반응식
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

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 70088Triethylenetetraminehexaacetic acidHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 4277N,N'-Dicyclohexylurea

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-2afdaad5e4ef4ac9be98e60a4c91f1a9
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021571

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