Sulfuric Acid → HCID 71179236, compound

HRID 1615031Notes

Reaction equation

HRID 1615031 reaction equation
OS(O)(=O)=O.Cl[CH2:7][CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:29][CH2:30][CH2:31][N:32]([CH2:45][CH3:46])[S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[N+:42]([O-:44])=[O:43])(=[O:35])=[O:34])[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([C:24](=[O:28])[CH2:25][CH2:26]Cl)=[CH:18][CH:17]=3)=[O:10]>C(Cl)Cl.C(OCC)(=O)C>[O:28]=[C:24]1[C:19]2[CH:18]=[CH:17][C:16]3[N:15]([CH2:29][CH2:30][CH2:31][N:32]([CH2:45][CH3:46])[S:33]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[N+:42]([O-:44])=[O:43])(=[O:34])=[O:35])[C:14]4[CH:13]=[CH:12][C:11]5[C:9](=[O:10])[CH2:8][CH2:7][C:23]=5[C:22]=4[C:21]=3[C:20]=2[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67366271HCID 67366271, compound

Product 1

HCID 71179236HCID 71179236, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

H2SO4 (110 mL) was heated to 40° C. Compound 61 (7.6 g, 12.3 mmol) was added in portions. The reaction mixture was heated to 100° C., kept at this temperature for 2 h (TLC monitoring, CH2Cl2/ethyl acetate 4:1), and poured into ice. The formed gray precipitate was filtered off. Then CHCl3/MeOH 4:1 (500 mL) was poured into the filter. The solid on the filter dissolved, and the formed solution was transferred into a separation funnel. An aqueous solution of Na2CO3 was added. The organic layer was separated, dried with Na7SO4, and evaporated. Acetonitrile was added to the residue. A beige precipitate was filtered off, washed with acetonitrile, with ether, and dried to give 1.56 g (23%) of a beige crystalline product.

Workup

  1. filtrationThe formed gray precipitate was filtered off
  2. additionThen CHCl3/MeOH 4:1 (500 mL) was poured into the filter
  3. dissolutionThe solid on the filter dissolved
  4. customthe formed solution was transferred into a separation funnel
  5. additionAn aqueous solution of Na2CO3 was added
  6. customThe organic layer was separated
  7. dry with materialdried with Na7SO4
  8. customevaporated
  9. additionAcetonitrile was added to the residue
  10. filtrationA beige precipitate was filtered off
  11. washwashed with acetonitrile, with ether
  12. customdried

Sources & evidence

ORD record
ord-e4d01fe0c4dd417fb081206e3e63decd
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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