Sulfuric Acid → HCID 136347216, compound

HRID 601121Notes

Reaction equation

HRID 601121 reaction equation
[O:1]=[S:2]1(=[O:31])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]([C:12]2[C:13](=[O:30])[N:14]([CH2:23][CH2:24][CH:25]3OCC[O:26]3)[C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:3]1.S(=O)(=O)(O)O>O.C(O)(=O)C>[O:31]=[S:2]1(=[O:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]([C:12]2[C:13](=[O:30])[N:14]([CH2:23][CH2:24][CH:25]=[O:26])[C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:3]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 136373917HCID 136373917, compound

Product 1

HCID 136347216HCID 136347216, compoundYield 761.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A stirred suspension of the product of Example 69B (0.65 g, 0.15 mmol) in water (3 mL) and glacial acetic acid (12 mL) at ambient temperature was treated dropwise with sulfuric acid (1 mL). The mixture was heated to 60° C. for 1 hour, and then diluted with water. The mixture was filtered and the filter cake was washed with water and dried to produce the title compound (0.455 g, 78%). MS (DCI/NH3) m/z 399 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.72 (m, 2H), 4.59 (t, J=6.62 Hz, 2H), 7.17 (dd, J=7.72, 4.78 Hz, 1H), 7.28 (m, 1H), 7.55 (m, 1H), 7.67 (d, J=7.72 Hz, 1H), 8.39 (dd, J=7.72, 1.84 Hz, 1H), 8.52 (dd, J=4.78, 1.84 Hz, 1H), 9.76 (t, J=2.21 Hz, 1H), 9.76 (t, J=2.21 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with water
  3. customdried

Sources & evidence

ORD record
ord-4a9483a0e8454535af3445ee69d75d90
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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