Methanesulfonyl chloride → HCID 19093827, compound

HRID 487315Notes

Reaction equation

HRID 487315 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][S:19][C:13]=3[CH:12]2[CH2:20][CH2:21][CH2:22][CH3:23])=[O:7])=[CH:4][CH:3]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(Cl)Cl.CO.[NH4+].[OH-]>>[CH2:20]([CH:12]1[C:13]2[S:19][CH:18]=[CH:17][C:14]=2[CH2:15][CH2:16][N:11]1[CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:25][CH:24]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 19093988HCID 19093988, compoundHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 19093827HCID 19093827, compoundYield 80%

Procedure

Prepared by Method F using the aminobenzene from Example 15 and methanesulfonyl chloride. The product was isolated as a white solid after flash silica gel chromatography using CH2Cl2 /Methanol/NH4OH (97.5/2.25/0.25 to 95.75/4/0.25). This material was recrystallized from EtOAc/ether to afford the title compound as an near-white solid (80%); mp 98°-105° C.; IR (KBr) 3420, 2930, 1635, 1610, 1553, 1505, 1340, 1310 and 1155 cm-1.

Workup

  1. customPrepared by Method F
  2. customThe product was isolated as a white solid after flash silica gel chromatography
  3. customThis material was recrystallized from EtOAc/ether

Sources & evidence

ORD record
ord-c24fecdeb04e4ade955bc7e31f26286d
Source dataset
uspto-grants-1994_03
Patent number
US05294621

Reaction notes

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