2-Naphthalenesulfonyl chloride → HCID 18779244, compound

HRID 1422306Notes

Reaction equation

HRID 1422306 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.C(N(CC)CC)C.[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1[S:47](Cl)(=[O:49])=[O:48]>ClCCl>[C:12]1([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:9]2[CH:10]=[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:47]([C:38]3[CH:39]=[CH:40][C:41]4[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:37]=3)(=[O:49])=[O:48])[N:7]=[CH:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 18779225HCID 18779225, compound

Product 1

HCID 18779244HCID 18779244, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from step c (465 mg, 1.22 mmol) and triethylamine (185 μl, 1.33 mmol) in dry dichloromethane (15 ml) was added 2-naphthalenesulfonyl chloride (227 mg, 1.22 mmol). The solution was stirred for 2 h and the solvent evaporated. Flash column chromatography (silica; 5% methanol/dichloromethane) of the residue afforded the product as a colourless foam (588 mg, 84%).

Workup

  1. customthe solvent evaporated

Sources & evidence

ORD record
ord-e84d2597586a4cd7985617857744e140
Source dataset
uspto-grants-2000_06
Patent number
US06080871

Reaction notes

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