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Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1845794
Notes
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Reaction equation

HRID 1845794 reaction equation
C(C(O)=[O:29])CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.ON1C(=O)CCC1=O.[CH:39]1([N:45]=[C:46]=[N:47][CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>C(OCC)(=O)C>[C:46]([NH:45][CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1)([NH:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1)=[O:29]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 27824134,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecanoic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2H,2H,3H,3H-Perfluoroundecanoic acid (1.354 g, 2.75 mmol), N-hydroxysuccinimide (348 mg, 3.02 mmol) and dicyclohexylcarbodiimide (622 mg, 3.02 mmol) were dissolved in ethyl acetate (120 ml) and stirred for 18 hours at ambient temperature. The white precipitate which formed (dicyclohexylurea, DCU) was filtered and the remaining solution was evaporated to dryness. The residue was recrystallised twice from ethyl acetate. Yield 1.00 g (62%) containing traces of DCU.

Sources & evidence

ORD record
ord-952f88a4056c4e999f06e406bcf45702
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08951630B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes