Tetrahydrofuran → N-(4-(1-adamantyl)-2-methylphenyl)-2-chloro-5-nitrobenzenesulfonamide

HRID 719760Notes

Reaction equation

HRID 719760 reaction equation
O1CCCC1.Cl.[C:7]12([C:17]3[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([CH3:24])[CH:18]=3)[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.C(N(CC)CC)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[S:42](Cl)(=[O:44])=[O:43]>O>[C:7]12([C:17]3[CH:23]=[CH:22][C:20]([NH:21][S:42]([C:34]4[CH:35]=[C:36]([N+:39]([O-:41])=[O:40])[CH:37]=[CH:38][C:33]=4[Cl:32])(=[O:44])=[O:43])=[C:19]([CH3:24])[CH:18]=3)[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][CH:11]([CH2:12]3)[CH2:16]1)[CH2:8]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 206302-Chloro-5-nitrobenzenesulfonyl chlorideHCID 163762694-(1-Adamantanyl)-2-methylaniline hydrochloride

Product 1

HCID 9955931N-(4-(1-adamantyl)-2-methylphenyl)-2-chloro-5-nitrobenzenesulfonamideYield 36.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 5 mL of a tetrahydrofuran solution comprising 250 mg of 4-(1-adamantyl)-2-methylaniline hydrochloride and 200 mg of triethylamine, 5 mL of a tetrahydrofuran solution comprising 230 mg of 2-chloro-5-nitrobenzenesulfonylchloride was dropwise added, followed by stirring at about 40° C. for about 7 hours. After the mixture was left to stand for cooling, water was added thereto, extraction with chloroform, drying over salt cake and concentration under reduced pressure were carried out to obtain crude crystals. The crude crystals were recrystalized from ether to obtain 150 mg of N-(4-(1-adamantyl)-2-methylphenyl)-2-chloro-5-nitrobenzenesulfonamide (Compound No. 48) having a melting point of 238° C.

Workup

  1. additionwas dropwise added
  2. waitAfter the mixture was left
  3. temperaturefor cooling
  4. extractionextraction with chloroform
  5. dry with materialdrying over salt cake and concentration under reduced pressure
  6. customto obtain crude crystals
  7. customThe crude crystals were recrystalized from ether

Sources & evidence

ORD record
ord-777acafa4f66488789b044b218be0731
Source dataset
uspto-grants-2006_11
Patent number
US07132546B2

Reaction notes

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