Sulfuric Acid → HCID 9843842, compound

HRID 1684107Notes

Reaction equation

HRID 1684107 reaction equation
S(=O)(=O)(O)O.[Cl:6][CH2:7][C:8]([NH:10][C:11]1[C:16]([C:17](=[O:20])[NH:18][CH3:19])=[C:15]([O:21][CH3:22])[C:14]([NH:23][C:24](=O)[CH2:25][Cl:26])=[C:13]([C:28](=[O:31])[NH:29][CH3:30])[C:12]=1[O:32][CH3:33])=O.C([O-])(=O)C.[Na+].[K+].[Br-]>C(OCC)(=O)C.CO.O.C(O)(=O)C>[Cl:26][CH2:25][C:24]1[N:29]([CH3:30])[C:28](=[O:31])[C:13]2[C:14]([N:23]=1)=[C:15]([O:21][CH3:22])[C:16]1[C:17](=[O:20])[N:18]([CH3:19])[C:8]([CH2:7][Cl:6])=[N:10][C:11]=1[C:12]=2[O:32][CH3:33]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 10003073HCID 10003073, compound

Product 1

HCID 9843842HCID 9843842, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution consisting of 15 mL of acetic acid and 0.5 mL of sulfuric acid, was added 333 mg (0.766 mmol) of 12. The resulting mixture was heated at 110° C. for 5.5 hours. After cooling the reaction mixture to room temperature, the solution was poured over ca 50 mL of water and then buffered to pH 6 with sodium acetate. The resulting yellow precipitate was filtered, washed with water, and then dried. The dried solid was recrystallized from ethanol: 219 mg (72%) yield; mp 273°-274° C.; TLC (ethyl acetate/methanol [9:1]), Rf =0.34; IR (KBr) 1677, 1607, 1434, 1347, 1324, 1269, 1071, 1032, 795, 690 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ4.92 (4H, s, methylenes), 3.95 (6H, s, methoxys), 3.59 (6H, s, 3- and 8- methyls); mass spectrum (EI), m/z 398 (P+, 35Cl35Cl), 400 (P+, 37Cl35Cl), 402 (P30, 37Cl37Cl37). Anal. Calcd for C16H16Cl2N4O4 : C, 48.14; H, 4.04; N, 14.03. Found: C, 48.40; H, 4.03; N, 14.14.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. filtrationThe resulting yellow precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customThe dried solid was recrystallized from ethanol
  6. custom219 mg (72%) yield

Sources & evidence

ORD record
ord-f297c3bce7de4b36b33b611b7bd0304b
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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