Dichloromethane → HCID 178527347, compound

HRID 15733Notes

Reaction equation

HRID 15733 reaction equation
C(Cl)Cl.S(Cl)(Cl)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][C:21]3=[N:24][NH:25][CH:26]=[C:20]3[CH:19]2[CH:27]=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[C:29]1([NH2:36])[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH2:35]>CCO>[NH:35]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:36]=[C:27]1[CH:19]1[C:20]2=[CH:26][NH:25][N:24]=[C:21]2[CH2:22][CH2:23][N:18]1[S:15]([C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7243O-PhenylenediamineHCID 24386Thionyl ChlorideHCID 178519238HCID 178519238, compound

Product 1

HCID 178527347HCID 178527347, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with silica (0.06 g) and CH2Cl2 (5 mL). Thionyl chloride (0.015 mL) was added dropwise. After the addition was complete, the reaction stirred at room temperature for 1 hour. Compound 79 (0.05 g, 0.15 mmol) was added, followed by phenylenediamine (0.017 g, 0.15 mmol). The reaction stirred at room temperature for 18 hours. The mixture was diluted with EtOH and the resulting suspension was filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by preparative HPLC using Method [1] to yield 7.8 mg (13%) 80 as a white powder. 1H NMR (CD3OD) δ 9.13 (s, 1H), 8.33 (s, 1H), 8.05-8.01 (m, 2H), 7.85-7.73 (m, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.39 (d, J=9.0 Hz), 3.42-3.34 (m, 3H); MS (m/z) 414.0 (M+H)+.

Workup

  1. additionAfter the addition
  2. stirringThe reaction stirred at room temperature for 18 hours
  3. filtrationthe resulting suspension was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5d2e3b9943e44a57b5193c1ac860a938
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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