Chloroacetyl chloride → HCID 53374094, compound

HRID 40771Notes

Reaction equation

HRID 40771 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:18].[Cl:19][CH2:20][C:21](Cl)=[O:22].C(OCC)(=O)C.CCCCCC>CN(C)C=O.CCO>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH:18][C:21](=[O:22])[CH2:20][Cl:19]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8058HexaneHCID 8857Ethyl AcetateHCID 156521,2-Diaminoanthraquinone

Product 1

HCID 53374094HCID 53374094, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

1,2-diaminoanthraquinone (1.19 g, 5 mmole) was dissolved in anhydrous N, N-dimethylformamide (30 ml). Nitrogen was insufflated in the reaction flask at room temperature. Chloroacetyl chloride (0.5 ml, 6 mmole) was added into the solution. The mixture was stirred at room temperature for 2 hours. After completion of reaction, the mixture was put in an ice-water bath (200 ml), and stood still for 10 to 20 minutes to allow precipitation. The precipitate was filtered and washed with hot ethanol to obtain a red compound CC-05. Mol. Wt.: 314.7231 (C16H11N2O3); Rf: 0.82 (ethyl acetate:n-hexane=1:4); Yield: 65%; Mp.: 193-194° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 314.0458 (C16H11N2O3+). Found, 314.0455. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 4.38 (s, 2H, —CH2Cl), 7.48 (d, J=7.8 Hz, 1H, Ar—H), 7.74 (d, J=8.1 Hz, 1H, Ar—H), 7.84 (dd, J=8.1 Hz, J=1.8 Hz, 1H, Ar—H), 7.88 (t, J=1.5 Hz, 1H, Ar—H), 7.91 (dd, J=7.5 Hz, J=1.5 Hz, 1H, Ar—H), 7.96 (br, 2H, Ar—NH2), 8.14 (dd, J=7.2 Hz, J=1.8 Hz, 1H, Ar—H), 8.22 (dd, J=7.8 Hz, J=1.5 Hz, 1H, Ar—H), 9.80 (s, 1H, Ar—NH—); 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 43.25, 112.98, 115.62, 126.69, 126.55, 129.88, 128.88, 128.92, 130.25, 131.01, 132.64, 133.65, 134.37, 165.72 (NCO), 182.28 (CO), 184.38 (CO).

Workup

  1. customwas insufflated in the reaction flask at room temperature
  2. customAfter completion of reaction
  3. customthe mixture was put in an ice-water bath
  4. wait(200 ml), and stood still for 10 to 20 minutes
  5. customprecipitation
  6. filtrationThe precipitate was filtered
  7. washwashed with hot ethanol
  8. customto obtain a red compound CC-05

Sources & evidence

ORD record
ord-0d179d0e5e6f43a9950b56af4e51d615
Source dataset
uspto-grants-2013_09
Patent number
US08530465B2

Reaction notes

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