Thionyl Chloride → HCID 58978242, compound

HRID 1180110Notes

Reaction equation

HRID 1180110 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:31])[C:23]4[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:34]>O1CCOCC1>[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([NH:21][C:22](=[O:31])[C:23]4[CH:28]=[CH:27][C:26]([CH2:29][Cl:34])=[CH:25][CH:24]=4)[CH:17]=[CH:18][C:19]=3[CH3:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58978203HCID 58978203, compound

Product 1

HCID 58978242HCID 58978242, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the solution of Example K (410 mg, 0.99 mmol) in 1,4-dioxane (40 mL) was slowly added SOCl2 (650 mg, 5.50 mmol) at RT. After being stirred at RT for 3 h, the solvent and excessive SOCl2 was removed in vacuo to yield N-(3-(4-phenylpyrimidin-2-ylamino)-4-methylphenyl)-4-(chloromethyl)benzamide as a yellow solid (460 mg), which was used without further purification. 1H NMR (CDCl3-d6) δ: 8.42 (s, 1H), 8.22 (d, J=6.0 Hz, 3H), 8.05 (m, 1H), 7.94 (d, J=1.0 Hz, 2H) 7.53-7.62 (m, 5H), 7.26 (s, 2H), 4.63 (d, J=5.4 Hz, 2H), 2.44 (s, 3H); MS (ESI) m/e: 429.20 (M++1)

Workup

  1. customat RT
  2. customthe solvent and excessive SOCl2 was removed in vacuo

Sources & evidence

ORD record
ord-c534b6db143241c39ad87eccb540674a
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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