Triethylamine → HCID 699697, compound

HRID 1749005Notes

Reaction equation

HRID 1749005 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[C:10](Cl)(=[O:13])[CH2:11][CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:13])[CH2:11][CH3:12])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97083-Chloro-4-fluoroanilineHCID 62324Propionyl chloride

Product 1

HCID 699697HCID 699697, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloro-4-fluoroaniline (10 g, 67.32 mmol) dissolved in CH2Cl2 was added with propionyl chloride (6.6 mL, 74.10 mmol) and triethyl amine (10.2 mL, 73.58 mmol) dropwise under water bath, and the mixture was stirred for 2 h. The resulting solution was washed with water (2×50 mL) and saturated aqueous NaHCO3 solution (12 mL). The CH2Cl2 layer dried over MgSO4 was evaporated to give title compound as light purple solid (13.01 g, 96.3%). 1H NMR (400 MHz, DMSO-d6) δ 1.06 (t, J=7.6 Hz, 3H), 2.30 (q, 7.6 Hz, 2H) 7.31 (dd, J=9.2 and 8.8 Hz, 1H), 7.44 (ddd, J=8.8 and 4 and 2.8 Hz, 1H), 7.91 (dd, J=7.2 and 2.8 Hz, 1H), 10.04 (br s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 9.4, 29.4, 116.6, 116.8, 118.8, 119.0, 119.1, 120.2, 136.55, 136.58, 151.5, 153.9, 172.1;

Workup

  1. washThe resulting solution was washed with water (2×50 mL) and saturated aqueous NaHCO3 solution (12 mL)
  2. dry with materialThe CH2Cl2 layer dried over MgSO4
  3. customwas evaporated

Sources & evidence

ORD record
ord-269f08673dbc4262bba6b927a4a3bf20
Source dataset
uspto-grants-2015_10
Patent number
US09155739B2

Reaction notes

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