Ethanol → HCID 54036314, compound

HRID 1066342Notes

Reaction equation

HRID 1066342 reaction equation
C(O)C.[CH2:4]([S:9]([NH:12][C:13](=[O:34])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([N:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[CH3:24])[CH:15]=1)(=[O:11])=[O:10])[CH2:5][CH2:6][CH2:7][CH3:8].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][S:9]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:11])=[O:10])=[O:34])=[CH:15][C:16]=1[N:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 86756985HCID 86756985, compound

Product 1

HCID 54036314HCID 54036314, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Four milliliters of ethanol and 4 ml of tetrahydrofuran were added to 0.605 g of N-(n-pentanesulfonyl)-3-(N-methy-2,4-dichlorobenzylamino)-4-nitrobenzamide, and subsequently 10 ml of an aqueous solution containing 3.10 g of sodium hydrosulfite was added thereto. The mixture was stirred at 80° C. for 20 minutes and then extracted with water and ethyl acetate. The organic layer was washed with water and concentrated. The resulting residue was crystallized from ether, filtrated, and dried to obtain 0.126 g of 4-amino-3-(N-methyl-2,4-dichlorobenzylamino)-(N-(n-pentanesulfonyl))benzamide (32).

Workup

  1. additionwas added
  2. extractionextracted with water and ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. customThe resulting residue was crystallized from ether
  6. filtrationfiltrated
  7. customdried

Sources & evidence

ORD record
ord-50062b4070af4b30aa59353e449ef6a1
Source dataset
uspto-grants-2001_06
Patent number
US06242474B1

Reaction notes

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