1,2-Dichloroethane → HCID 9838248, compound

HRID 432872Notes

Reaction equation

HRID 432872 reaction equation
C(O[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH2:10]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[Cl:23]CCCl.O(C([NH:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)=O)C1C=CC=CC=1>C1(OC)C=CC=CC=1.ClCCl.C(N(CC)CC)C>[ClH:23].[CH3:15][C:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:6]([NH:36][C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[O:7])[CH2:10][CH:11]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 22171687HCID 22171687, compound

Product 1

HCID 9838248HCID 9838248, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-tert-butoxycarbonylamino-4-methylcyclohex-3-ene (0.18 g) in a mixture of anisole (0.18 ml) and dichloromethane (0.36 ml) was added trifluoroacetic acid (0.54 ml) at 0° C. and the mixture was allowed to stir at 0° C. for 1 hour. Evaporation gave a residue, which was taken up into 1,2-dichloroethane (5 ml). To the mixture were added triethylamine (0.6 ml) and 4-phenoxycarbonylaminopyridine (0.183 g), and the resultant mixture was heated to 75° C. for 6 hours. Evaporation gave a residue, which was chromatographed on silica gel (50 ml) eluting with 7% methanol in dichloromethane, and taken up into a solution of hydrogen chloride in ethyl acetate (4N, 2 ml). Evaporation under reduced pressure and trituration with diisopropyl ether gave N-(4-methylcyclohex-3-en-1-yl)-N′-(pyridin-4-yl)urea hydrochloride (0.144 g).

Workup

  1. customEvaporation
  2. customgave a residue, which
  3. customEvaporation
  4. customgave a residue, which
  5. customwas chromatographed on silica gel (50 ml)
  6. washeluting with 7% methanol in dichloromethane
  7. customEvaporation under reduced pressure and trituration with diisopropyl ether

Sources & evidence

ORD record
ord-97b333d02d1147fc9d4ebb555c1277d3
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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