4-Chlorobenzenesulfonyl chloride → HCID 22099461, compound

HRID 1457577Notes

Reaction equation

HRID 1457577 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([NH2:31])[C:12](=[O:30])[NH:13][C:14]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:15]=1[O:16][CH2:17][O:18][CH3:19])=[O:5])[CH3:2].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([NH:31][S:39]([C:36]1[CH:37]=[CH:38][C:33]([Cl:32])=[CH:34][CH:35]=1)(=[O:41])=[O:40])[C:12](=[O:30])[NH:13][C:14]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([C:26]([CH3:27])([CH3:29])[CH3:28])[C:15]=1[O:16][CH2:17][O:18][CH3:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 22099504HCID 22099504, compound

Product 1

HCID 22099461HCID 22099461, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5 g of {2-[3-(5-ethoxycarbonylpentyl)-3-aminoureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane, 5 g of 4-chlorobenzenesulfonyl chloride, 7.24 g of triethylamine and 20 ml of chloroform was refluxed for 4 hours. The solvent was removed under reduced pressure. Ethyl acetate was added to the residue and the mixture was washed and dried, and the solvent was removed under reduced pressure to give 4 g of {2-[3-(5-ethoxycarbonylpentyl)-3-(4-chlorobenzenesulfonylamino)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane (yield: 57%, state: oily product, IR (film): 3400, 1732, 1710, 1610, 1590 cm-1).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was removed under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washthe mixture was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b1abb7c9e3714839badb853998e62ffc
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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