Chloroform → HCID 22316582, compound

HRID 241889Notes

Reaction equation

HRID 241889 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[Cl:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].C(Cl)(Cl)Cl>C1C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[Cl:16])=[O:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 72402-ChloroanilineHCID 24386Thionyl ChlorideHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 22316582HCID 22316582, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-4-fluorobenzoic acid (1.15 g, 7.41 mmol) and SOCl2 (1.4 mL, 18.5 mmol) in benzene (25 mL), followed by 2-chloroaniline (1.6 mL, 14.8 mmol) and CHCl3 (25 mL). The product was chromatographed in CH2Cl2, then triturated from hexanes to provide 1.02 g of an off-white solid (52%). 1H NMR (CDCl3) δ: 12.91 (br s, 1H); 8.72 (dd, J=2.7, 12 Hz, 1H); 8.34 (dd, J=6.4, 9.2 Hz, 1H); 8.29 (dd, J=5.9, 8.8 Hz, 1H); 7.81 (dd, J=6.2, 8.8 Hz, 1H); 7.28 (dt, J=2.4, 8.4 Hz, 1H); 7.21 (dd, J=2.4, 9.0 Hz, 1H); 6.92 (ddd, J=2.4, 7.3, 9.1 Hz, 1H); 6.54 (ddd, J=2.4, 7.8, 8.8 Hz, 1H); 6.45 (dd, J=2.4, 11 Hz, 1H); 5.93 (br s, 2H). MS (ES): m/z 265.0 (M+).

Workup

  1. customPrepared
  2. customThe product was chromatographed in CH2Cl2
  3. customtriturated from hexanes

Sources & evidence

ORD record
ord-eca8f8659f734909b70cee73e3a303e1
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Reaction notes

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