Benzylamine → HCID 54239113, compound

HRID 612384Notes

Reaction equation

HRID 612384 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([S:16](Cl)(=[O:18])=[O:17])[CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.N1C=CC=CC=1>[CH2:25]([NH:32][S:16]([C:7]1[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([O:4][C:3]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:2]=2[Cl:1])[CH:6]=1)(=[O:18])=[O:17])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 23221647HCID 23221647, compound

Product 1

HCID 54239113HCID 54239113, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(2,4-Dichlorophenoxy)-4-methylsulphonylaminobenzene-sulphonic acid chloride (1.08 g, 2.51 mmol) was dissolved in CH2Cl2 (5 ml) and at 0° C. added dropwise to a solution of benzylamine (0.35 ml, 3.2 mmol) in pyridine (20 ml). The mixture was stirred for 2 hours at 0° C. and then evaporated down. The residue was dried in vacuo and purified by chromatography (silica gel, CHCl3 /MeOH 19/1). Yield: 0.18 g=15% 13C (100 MHz, DMSO-d6) δ 149.94, 147.70, 137.38, 137.26, 132.04, 130.41, 129.55, 129.19, 128.30, 127.71, 127.28, 126.23, 123.52, 122.87, 122.67, 114.71, 46.23, 40.92

Workup

  1. customevaporated down
  2. customThe residue was dried in vacuo
  3. custompurified by chromatography (silica gel, CHCl3 /MeOH 19/1)

Sources & evidence

ORD record
ord-a31f41a36fa1404d831f2e51365bd083
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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