Dichloroacetyl chloride → HCID 67167119, compound

HRID 874713Notes

Reaction equation

HRID 874713 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([C:14]3[CH:20]=[C:19]([C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=[CH:17][C:15]=3[NH2:16])=[O:13])=[CH:8][CH:7]=2)[N:5]=[N:4]1.[Cl:29][CH:30]([Cl:34])[C:31](Cl)=[O:32]>C(Cl)Cl>[Cl:29][CH:30]([Cl:34])[C:31]([NH:16][C:15]1[CH:17]=[CH:18][C:19]([C:21]#[C:22][Si:23]([CH3:24])([CH3:26])[CH3:25])=[CH:20][C:14]=1[C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:3]2([C:2]([F:1])([F:27])[F:28])[N:5]=[N:4]2)=[CH:7][CH:8]=1)=[O:13])=[O:32]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 67167864HCID 67167864, compound

Product 1

HCID 67167119HCID 67167119, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-({4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}carbonyl)-4-[2-(trimethylsilyl)ethynyl]aniline (47 mg, 0.12 mmol, 1 eq.) was dissolved in DCM (10 mL) and cooled to 0° C. Dichloroacetyl chloride (0.013 mL, 0.14 mmol, 1.15 eq.) was then added, and the reaction was stirred at 0° C. for 10 minutes. The reaction was then warmed to room temperature and stirred for 30 minutes. The solvent was evaporated, and the residue was purified by silica column (hexanes/ethyl acetate, 3:1), resulting in 57 mg (94%) of the title compound as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 11.83 (s, 1H, CHCl2), 8.56 (d, J=8.7, 1H, Ar—H), 7.76 (d, J=9.1, 2H, Ar—H), 7.69 (dd, J=1.5, 8.8, 1H, Ar—H), 7.61 (d, J=1.8, 1H, Ar—H), 7.32 (d, J=8.2, 2H, Ar—H), 6.03 (s, 1H, NH), 0.19 (s, 9H, Si(CH3)3). 13C NMR (126 MHz, CDCl3) δ 197.81 (Ar2—CO), 163.13 (NCOC), 139.23 (C—Ar), 138.79 (C—Ar), 138.33 (C—Ar), 136.61 (C—Ar), 134.08 (C—Ar), 130.47 (C—Ar), 126.71 (q, J=1.23, C—Ar), 123.41 (C—Ar), 122.03 (q, J=274.68, CF3), 121.60 (C—Ar), 120.94 (C—Ar), 103.04 (CSi(CH3)3), 96.22 (CCSi(CH3)3), 67.16 (CCl2), 28.64 (q, J=40.83, CN2), 0.03 (Si(CH3)3). Exact Mass, 511.05. 509.4841 [M−H]−, 511.487 [M+H]+.

Workup

  1. temperatureThe reaction was then warmed to room temperature
  2. stirringstirred for 30 minutes
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica column (hexanes/ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-b4ece2234c0046fc84746accb98b3c40
Source dataset
uspto-grants-2015_03
Patent number
US08980926B2

Reaction notes

Loading…