Diethyl Ether → HCID 19830007, compound

HRID 1493589Notes

Reaction equation

HRID 1493589 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:37]=[CH:36][C:17]([O:18][CH2:19][C:20]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=4[Cl:35])([OH:27])[CH2:21][N:22]4[CH:26]=[N:25][CH:24]=[N:23]4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:46]([O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:47].CCOCC>C(Cl)Cl>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[C:20]([OH:27])([CH2:19][O:18][C:17]1[CH:36]=[CH:37][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:46]([O:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)=[O:47])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:15][CH:16]=1)[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 15891Phenyl chloroformate2×HCID 14986929HCID 14986929, compound

Product 1

HCID 19830007HCID 19830007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(4-[4-(4-aminophenyl)piperazin-1-yl]phenoxy)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (see Preparation 1) (0.5 g, 0.93 mmole) and triethylamine (0.16 g, 1.6 mmole) in methylene chloride (20 ml) at 0° was added, dropwise, a solution of phenyl chloroformate (0.16 g, 1.02 mmole) in methylene chloride (2 ml). After 1 hour at 0°, an additional portion of phenyl chloroformate (0.05 g, 0.32 mmole) was added and stirring continued for a further 0.5 hour. The reaction was subsequently quenched by the addition of 2N sodium hydroxide solution, methylene chloride added, the organic phase separated, washed with water, dried over magnesium sulphate and concentrated under reduced pressure to yield a foam. Trituration of this foam with ether yielded the desired product as a buff solid, (0.42 g, 68%), which was used without further purification.

Workup

  1. waitcontinued for a further 0.5 hour
  2. customThe reaction was subsequently quenched by the addition of 2N sodium hydroxide solution, methylene chloride
  3. additionadded
  4. customthe organic phase separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customto yield a foam

Sources & evidence

ORD record
ord-68bbbb3f40b947fd8e536c9f45475d22
Source dataset
uspto-grants-1991_06
Patent number
US05023258

Reaction notes

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