Dimethylformamide → HCID 15795689, compound

HRID 1777080Notes

Reaction equation

HRID 1777080 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:16]=[C:15]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14]2)[CH:8]=1.CN(C)[CH:19]=[O:20]>>[CH3:6][C:7]1[CH:8]=[C:9]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=[CH:10]2)[C:16]=1[CH:19]=[O:20]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 111263792-methylazulene

Product 1

HCID 15795689HCID 15795689, compound

Procedure

POCl3 (3.86 mL, 42.2 mmol) was added slowly to a stirring dimethylformamide (DMF) solution at 0° C. The mixture was cooled for 1 h before a DMF solution of 2-methyl azulene (2.0 g, 14.1 mmol) was added drop-wise. The reaction was mixed for 2 h at 0° C., and then quenched with cold 10% NaOH. The organic layer was extracted into ethyl acetate after which the extracts were washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a dark red solid. Yield: 2.389 g, 89%. 1H NMR (400 MHz, CDCl3) δ 10.50 (s, 1H), 9.44 (d, J=9.73 Hz, 1H), 8.29 (d, J=9.72 Hz, 1H), 7.72 (t, J=9.82 Hz, 1H), 7.56 (t, J=9.82 Hz, 1H), 7.46 (t, J=9.67 Hz, 1H), 7.08 (s, 1H), 2.84 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 185.8, 154.9, 144.4, 142.1, 137.9, 136.4, 129.7, 128.5, 122.5, 120.3, 15.1. HRMS (ES) calcd. MH+(C12H11O) 171.0732 found 171.0804.

Workup

  1. additionwas added drop-wise
  2. additionThe reaction was mixed for 2 h at 0° C.
  3. customquenched with cold 10% NaOH
  4. extractionThe organic layer was extracted into ethyl acetate after which the extracts
  5. washwere washed with water and brine
  6. dry with materialdried with MgSO4
  7. custompurified
  8. customThe purified material was dried down into a dark red solid

Sources & evidence

ORD record
ord-a180d4e6465744dba3e4237c960327a9
Source dataset
uspto-grants-2016_02
Patent number
US09266847B2

Reaction notes

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