Benzoyl chloride → HCID 20376330, compound

HRID 2052698Notes

Reaction equation

HRID 2052698 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.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N(CC)(CC)CC.Cl>C(Cl)Cl.CCOCC.O>[C:29]([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:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 12519123HCID 12519123, compound

Product 1

HCID 20376330HCID 20376330, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred mixture, under N2, of 12.6 g of 1-(2-amino-4-trifluoromethylphenyl)indoline hydrochloride in 150 ml of dry CH2Cl2 is treated with 8.09 g of triethylamine. The mixture is cooled to 0°-5° C., and kept at that temperature while a solution of 5.62 g of benzoyl chloride and 25 ml of CH2Cl2 is added dropwise over 1.0 hour. After stirring at room temperature overnight, water is added to dissolve (C2H5)3N.HCl and the layers are separated. The organic phase is extracted further with water, 3 N--HCl, 3 N--NaOH, water again and dried over N2SO4. The solvent is removed leaving an oil which, when digested with ether, becomes a crystalline mass. After cooling, 1-(2-benzamido-4-trifluoromethylphenyl)indoline is obtained having m.p. 114°-119° C.

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. additionis added dropwise over 1.0 hour
  3. customthe layers are separated
  4. extractionThe organic phase is extracted further with water, 3 N
  5. dry with materialHCl, 3 N--NaOH, water again and dried over N2SO4
  6. customThe solvent is removed
  7. customleaving an oil which, when
  8. temperatureAfter cooling

Sources & evidence

ORD record
ord-042296ec7a934cf58c4b59b0e97554e9
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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