Triethylamine → HCID 20376336, compound

HRID 2052699Notes

Reaction equation

HRID 2052699 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].N(CC)(CC)CC.Cl>C(Cl)Cl.C(O)C.O>[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([NH:2][C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:5][C:4]=1[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1)=[O:33]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 11130Triethylamine hydrochlorideHCID 12519123HCID 12519123, compound

Product 1

HCID 20376336HCID 20376336, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture, under N2, of 10.2 g of 1-(2-amino-4-trifluoromethylphenyl)indoline hydrochloride in 100 ml of dry methylene chloride is added 7.08 g of triethylamine. The mixture is cooled to 0°-5° C., and kept at that temperature while a solution of 5.71 g of o-fluorobenzoyl chloride in 50 ml of dry methylene chloride is added dropwise over 1 hour. After stirring at room temperature overnight, water is added to dissolve the precipitated (C2H5)3N.HCl salt, and the layers are separated. The organic phase is washed further with 3 N--HCl, 3 N--NaOH, with water and dried over sodium sulfate. The solvent is removed leaving an oil which is dissolved in 25 ml of ethanol and sets solid on cooling. The crystals are collected, washed with ethanol, and dried to afford 1-[2'-(2-fluorobenzoylamino)-4'-trifluoromethylphenyl]indoline, m.p. 127°-130° C.

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. additionis added dropwise over 1 hour
  3. customthe layers are separated
  4. washThe organic phase is washed further with 3 N
  5. dry with materialHCl, 3 N--NaOH, with water and dried over sodium sulfate
  6. customThe solvent is removed
  7. customleaving an oil which
  8. temperatureon cooling
  9. customThe crystals are collected
  10. washwashed with ethanol
  11. customdried

Sources & evidence

ORD record
ord-d99d0ee195184f0e9518db6cec5dfabe
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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