Chloroform → HCID 22316574, compound

HRID 241901Notes

Reaction equation

HRID 241901 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)([O-:3])=[O:2].O=S(Cl)Cl.[Cl:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21].C(Cl)(Cl)Cl>C1C=CC=CC=1>[NH2:13][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=1[C:8]([NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[Cl:18])=[O:10]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 72402-ChloroanilineHCID 120764-Nitroanthranilic acidHCID 24386Thionyl Chloride

Product 1

HCID 22316574HCID 22316574, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 4-nitroanthranilic acid (5.0 g, 27.5 mmol) and SOCl2 (5.0 mL, 68.6 mmol) in benzene (150 mL), followed by 2-chloroaniline (5.8 mL, 55.0 mmol) and CHCl3 (150 mL). The product was purified by chromatography in CH2Cl2 followed by recrystallization from MeOH to provide 2.20 g of an orange-brown solid (31%). 1H NMR (CDCl3) δ: 8.41 (dd, J=1.3, 8.3 Hz, 1H); 8.31 (br s, 1H); 7.67 (d, J=8.6 Hz, 1H); 7.57 (d, J=2.1 Hz, 1H); 7.52 (dd, J=2.2, 8.5 Hz, 1H); 7.44 (dd, J=1.3, 8.1 Hz, 1H); 7.35 (dt, J=1.3, 7.9 Hz, 1H); 7.13 (dt, J=1.4, 7.8 Hz, 1H); 5.88 (br s, 2H). MS (ES): m/z 292.0 (M+).

Workup

  1. customPrepared
  2. customThe product was purified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from MeOH

Sources & evidence

ORD record
ord-89a642baebf1482cb71607bd8f96116b
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Reaction notes

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