Triethylamine → HCID 118107769, compound

HRID 1773470Notes

Reaction equation

HRID 1773470 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[I:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[CH3:21])[NH2:17].CCN(CC)CC.[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]2[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][C:38]=2[C:44]([F:47])([F:46])[F:45])[CH2:32][CH2:31]1>C(Cl)CCl>[I:13][C:14]1[CH:15]=[C:16]([NH:17][C:5]([NH:41][C:40]2[CH:42]=[CH:43][C:37]([CH2:36][N:33]3[CH2:32][CH2:31][N:30]([CH3:29])[CH2:35][CH2:34]3)=[C:38]([C:44]([F:47])([F:46])[F:45])[CH:39]=2)=[O:11])[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429Triphosgene2×HCID 1188893-Iodo-p-toluidineHCID 46838908AP-24592

Product 1

HCID 118107769HCID 118107769, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Triphosgene (1.04 g, 3.5 mmol) and ClCH2CH2Cl (20 ml) were added into a 100 ml round-bottomed flask, and stirred at room temperature until triphosgene was completely dissolved and the system appears colorless and transparent. The reaction system was placed in an ice-salt bath and stirred, 3-iodo-4-methylaniline (1.64 g, 7 mmol) in ClCH2CH2Cl solution (20 ml) was slowly added dropwise, and the system appears yellow milky. After the addition was complete, the mixture was stirred at room temperature for 4 hours. Et3N (1.43 g, 14 mmol) was added and stirred at room temperature for 0.5 hour. 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline (1.87 g, 7 mmol) was added and stirred at room temperature for 16 hours. The volatiles were removed by distillation under reduced pressure, and the residue was extracted with ethyl acetate (30 ml×3) and H2O (30 ml). The organic phases were combined, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography, to give a yellow solid.

Workup

  1. dissolutionwas completely dissolved
  2. customThe reaction system was placed in an ice-salt bath
  3. additionAfter the addition
  4. stirringthe mixture was stirred at room temperature for 4 hours
  5. stirringstirred at room temperature for 0.5 hour
  6. stirringstirred at room temperature for 16 hours
  7. customThe volatiles were removed by distillation under reduced pressure
  8. extractionthe residue was extracted with ethyl acetate (30 ml×3) and H2O (30 ml)
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. custompurified by column chromatography
  12. customto give a yellow solid

Sources & evidence

ORD record
ord-dad23e61e2664431a0c8d02319ca915f
Source dataset
uspto-grants-2016_02
Patent number
US09255107B2

Reaction notes

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