Acetic Anhydride → HCID 11667371, compound

HRID 2425132Notes

Reaction equation

HRID 2425132 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1.ClCCl>[C:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:15][C:10]([S:7]([NH:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:22](=[O:24])[CH3:23])(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11601917N-(4-aminobutyl)biphenyl-4-sulfonamide

Product 1

HCID 11667371HCID 11667371, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Biphenyl-4-sulfonic acid (4-amino-butyl)amide (1 g) was suspended in a mixture of acetic anhydride (45 mL) and pyridine (15 mL) and stirred at 80° C. for 4 hours. The solution was left to stir overnight and then poured into ice water. The aqueous mixture was extracted with dichloromethane, dried (Na2SO4) and evaporated to give a brown oil. The oil was redissolved in dichloromethane and the title compound precipitated as a white solid by addition of a small amount of petrol. δC (CDCl3, 62.9 MHz): 23.2, 26.6, 26.8, 39.1, 42.9, 127.3, 127.6, 127.8, 128.5, 129.1, 138.4, 139.3, 145.6 and 170.9.

Workup

  1. waitThe solution was left
  2. stirringto stir overnight
  3. extractionThe aqueous mixture was extracted with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a brown oil
  7. customthe title compound precipitated as a white solid by addition of a small amount of petrol

Sources & evidence

ORD record
ord-ecd4eb58c72b448e8e13a5a357b3cc6b
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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