Water → HCID 33730957, compound

HRID 2265171Notes

Reaction equation

HRID 2265171 reaction equation
N[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](Cl)(Cl)=[O:14].CC[N:19](C(C)C)C(C)C.O>C(Cl)Cl.C1COCC1>[Cl:12][C:8]1[C:9]([Cl:11])=[CH:10][CH:2]=[C:3]2[C:4]([O:6][C:13](=[O:14])[NH:19][C:7]=12)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 121045502-Amino-4,5-dichlorobenzoic acid

Product 1

HCID 33730957HCID 33730957, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4,5-dichloro-benzoic acid (1.5 g, 7.28 mmol) was dissolved in 1:1 DCM/THF (20 mL) and cooled to 0° C. Phosgene (20% in toluene, 5.4 mL, 8.00 mmol) and Hünig's base (2.54 mL, 14.6 mmol) were added and the reaction was stirred overnight and warmed slowly to rt. The mixture was poured into water and extracted with DCM (3×) and EtOAc (2×). The combined organic layers were dried (MgSO4), and concentrated to provide the product as a white solid (1.6 g, 92%). HPLC: RT=8.10 min. MS (ESI−): mass calcd. for C8H3Cl2NO3, 232.0; m/z found, 231 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 11.95 (s, 1H), 8.10 (s, 1H), 7.32 (s, 1H).

Workup

  1. temperaturewarmed slowly to rt
  2. extractionextracted with DCM (3×) and EtOAc (2×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79a2415d81ba453c9382e5765c3e2182
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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