Water → HCID 9863218, compound

HRID 2121735Notes

Reaction equation

HRID 2121735 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([O:21]CC)=[O:20])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:33](Cl)(Cl)=[O:34].O>C1(C)C=CC=CC=1.C(OCC)C>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([OH:21])=[O:20])[C:33]2=[O:34])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 10269420HCID 10269420, compound

Product 1

HCID 9863218HCID 9863218, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-(3-trifluoromethylphenyl)-N′-(2-ethyloxycarbonylphenyl)-1,2-diaminoethane (1.1 g, 3.1 mmol) and triethylamine (1.1 mL, 7.5 mmol) in toluene was added phosgene in toluene (1.84 mL, 3.5 mmol). After stirring at room temperature for 30 min. Water and diethyl ether were added. The organic phase was dried and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel using dichloromethane as eluent. The isolated ester (0.96 g) was hydrolysed in 4N aqueous sodium hydroxide to give the desired compound in a yield of 0.6 g. M.p. 197-198° C.

Workup

  1. customThe organic phase was dried
  2. customevaporated to dryness
  3. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-54b8668c141244b8bba27e749c7dde83
Source dataset
uspto-grants-2004_02
Patent number
US06696475B2

Reaction notes

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