Acetic Acid → HCID 67614195, compound

HRID 1417329Notes

Reaction equation

HRID 1417329 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:26]=[CH:30][CH:29]=[CH:28]3)=[CH:21][CH:22]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 67598281HCID 67598281, compound

Product 1

HCID 67614195HCID 67614195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of 3.2 g of 4-methyl-N-[4-(4-aminophenyl-oxy)butyl]benzenesulfonamide (Example 36), 1.5 g of 2,5-dimethoxytetrahydrofuran, and 50 ml of acetic acid is stirred and heated on the steam bath for 16 hours. The reaction mixture is taken to dryness in vacuo. The residue is shaken with 150 ml of dichloromethane and 150 ml of saturated sodium bicarbonate solution. The dichloromethane layer is separated, dried over Na2SO4, and diluted with 100 ml of hexane. The solution is concentrated until turbid, then cooled at -10° C. The precipitate that forms is collected, washed with hexane, and air dried; m.p. 124°-126° C.; yield, 0.2 g.

Workup

  1. temperatureheated on the steam bath for 16 hours
  2. customThe dichloromethane layer is separated
  3. dry with materialdried over Na2SO4
  4. additiondiluted with 100 ml of hexane
  5. concentrationThe solution is concentrated until turbid
  6. customThe precipitate that forms is collected
  7. washwashed with hexane, and air
  8. customdried
  9. customyield

Sources & evidence

ORD record
ord-83f0486d4e7b4b7caca88a19da94a133
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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