Methanol → HCID 58399162, compound

HRID 641707Notes

Reaction equation

HRID 641707 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:25])[CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([CH:23]=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28].[CH3:32][OH:33]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:25])[CH:12]2[CH2:24][N:16]3[C:17]4[C:22]([C:23]([C:26](=[O:30])[C:27]([O:33][CH3:32])=[O:28])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 58399171HCID 58399171, compound

Product 1

HCID 58399162HCID 58399162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.9 g of the product of Step 9 in 50 mL of CH2Cl2 was added 0.42 mL of oxalyl chloride at 0° C. After stirring for 1 h at 0° C., 4 mL of MeOH was added and the mixture was stirred for another hour and quenched with 30 mL of saturated aqueous solution of NaHCO3. The mixture was extract with 50 mL of CH2Cl2 and the extract was dried over Na2SO4. After filtration, the filtrated was concentrated to give 1.2 of the title product as a solid. 1H NMR (500 MHz, acetone-d6) d 8.11 (m, 2H), 7.92 (m, 1H), 7.45-7.52 (m, 3H), 7.28-7.34 (m, 2H, 4.70 (m, 1H), 7.32 (m, 1H), 4.12 (t, 1H), 3.97 (s, 3H), 3.48-3.55 (m, 1H), 3.08-3.07 (m, 1H), 3.00 (s, 3H), 2.10 (m, 1H), 1.76 (m, 1H).

Workup

  1. stirringthe mixture was stirred for another hour
  2. customquenched with 30 mL of saturated aqueous solution of NaHCO3
  3. extractionThe mixture was extract with 50 mL of CH2Cl2
  4. dry with materialthe extract was dried over Na2SO4
  5. filtrationAfter filtration
  6. concentrationthe filtrated was concentrated

Sources & evidence

ORD record
ord-d3e21e2f9bc74f0b9a8a8150c0cfdb6c
Source dataset
uspto-grants-2010_04
Patent number
US07696222B2

Reaction notes

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