Water → HCID 178426856, compound

HRID 40490

Reaction equation

HRID 40490 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH:16]1[C:21]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=[C:18]([N:28]([CH2:32][CH2:33][Cl:34])[CH2:29][CH2:30][Cl:31])[CH:17]=1.[CH3:35][C:36]1([CH3:46])[N:41]([O:42])[C:40]([CH3:44])([CH3:43])[CH2:39][CH:38]([OH:45])[CH2:37]1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:20]1[C:21]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:16][CH:17]=[C:18]([N:28]([CH2:29][CH2:30][Cl:31])[CH2:32][CH2:33][Cl:34])[CH:19]=1.[CH3:35][C:36]1([CH3:46])[N:41]([O:42])[C:40]([CH3:44])([CH3:43])[CH2:39][CH:38]([OH:45])[CH2:37]1

Participants

7

Reactant 4

HCID 962WaterHCID 2708Chlorambucil2×HCID 10868Dicyclohexylcarbodiimide2×HCID 137994Tempol2×

Product 1

HCID 178426856HCID 178426856, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

DCC coupling reaction was used to couple the carboxylic group of chlorambucil with the hydroxyl group of TEMPOL with the loss of a water molecule. To a stirred solution of TEMPOL (0.172 g, 1 mmol) and chlorambucil (0.304 g, 1 mmol) in methylene chloride (5 ml) at 0° C. under argon, DCC (0.206 g, 1 mmol) (Dicyclohexyl carbodiimide) and DMAP (0.0307 g, 0.25 mmol) (Dimethyl amino pyridine) were added and the reaction mixture was stirred for 12 hrs at room temperature. The solid materials formed were filtered off, and the filtrate was washed with 1 M HCl (1 ml) followed by saturated NaHCO3 (2 ml) and brine (2 ml). The organic phase was dried over MgSO4 and evaporated in vacuum to give 0.4 g of CT corresponding to a yield of 87%. TLC (Thin Layer Chromatography) of the product showed a single spot only.

Workup

  1. customThe solid materials formed
  2. filtrationwere filtered off
  3. washthe filtrate was washed with 1 M HCl (1 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated in vacuum
  6. customto give 0.4 g of CT corresponding to a yield of 87%

Sources & evidence

ORD record
ord-633ce97e39b945cbbbe4136863d78fed
Source dataset
uspto-grants-2013_09
Patent number
US08530434B2

Linked notes

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