Triethylamine → ST005495

HRID 528837Notes

Reaction equation

HRID 528837 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[Cl:20])[C:14](Cl)=[O:15].CCN(CC)CC>CC#N>[Cl:10][C:11]1[CH:12]=[C:13]([C:14]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:15])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10328IndolineHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 673639ST005495Yield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of indoline (2.0 mL, 17.8 mmol) in MeCN (45.0 mL) was added 3,4-dichlorobenzoyl chloride (4.11 g, 19.6 mmol) followed by Et3N (7.5 mL, 53.5 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h and then concentrated in vacuo. The residue was triturated with water and dried under high vacuum to give the title compound (5.2 g, 100%) as a light brown solid. 1H NMR (DMSO-d6) δ 7.89 (d, J=1.1 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.29 (d, J=7.3 Hz, 1H), 7.19 (m, 1H), 7.06 (t, J=7.2 Hz, 1H), 4.00 (t, J=8.3 Hz, 2H), 3.09 (t, J=8.3 Hz, 2H); MS(ESI+) m/z 292.1 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-50c78d3da38747ada3cdf169b4b3f42a
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…