Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1938781Notes

Reaction equation

HRID 1938781 reaction equation
[OH:1]C(P(O)O)(C1C=CC(C)=CC=1)C.ClCC(O)C.CN(C1C=CC=CN=1)C.[CH:28]1([N:34]=[C:35]=[N:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>O1CCCC1.CCOCC>[C:35]([NH:34][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)([NH:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)=[O:1]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 313701-Chloro-2-propanolHCID 21469988HCID 21469988, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-hydroxy-1-p-tolylethylphosphonous acid (0.2 g., 0.01M), 1-chloro-2-propanol (0.094 g., 0.01M) and dimethylaminopyridine (0.01 g) are stirred in tetrahydrofuran (5 ml.) at 5° C. Dicyclohexylcarbodiimide (0.23 g., 0.001M) is added portionwise over 1 hour. On completion of the reaction (monitored by 31P NMR) ether (10 ml) is added and the dicylohexylurea formed is filtered off. Evaporation of the filtrate gives an oil which is purified by chromatography on silica using 5% methanol in chloroform as eluant. There is obtained 1-chloromethylethyl (1-hydroxy-1-p-tolylethyl) phosphinate.

Workup

  1. additionis added

Sources & evidence

ORD record
ord-9b135a815daa4dff88705bbd2b63dbd8
Source dataset
uspto-grants-1997_12
Patent number
US05693799

Reaction notes

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