(Methylazanediyl)dimethanol → HCID 67596959, compound

HRID 612385Notes

Reaction equation

HRID 612385 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].OCN([CH2:29][OH:30])C>C(Cl)Cl.N1C=CC=CC=1>[OH:4][CH2:5][CH:10]([CH2:29][OH:30])[NH:11][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]

Participants

5

Reactant 2

HCID 14205709(Methylazanediyl)dimethanolHCID 23221647HCID 23221647, compound

Product 1

HCID 67596959HCID 67596959, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(2,4-Dichlorophenoxy)-4-methylsulphonylaminobenzene-sulphonic acid chloride (1.8 g, 2.51 mmol) was dissolved in CH2Cl2 (5 ml) and at 0° C. added dropwise to a solution of bis(hydroxymethyl)methylamine (0.44 g, 4.8 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, chloroform/MeOH 19/1) Yield: 0.35 g=29% 13C (100 MHz, DMSO-d6) δ 150.17, 147.50, 138.39, 132.09, 130.34, 129.29, 129.10, 126.02, 123.25, 122.75, 122.51, 115.22, 60.36, 57.07, 40.94

Workup

  1. customevaporated down
  2. customThe residue was dried in vacuo
  3. custompurified by chromatography (silica gel, chloroform/MeOH 19/1) Yield: 0.35 g=29% 13C (100 MHz, DMSO-d6) δ 150.17, 147.50, 138.39, 132.09, 130.34, 129.29, 129.10, 126.02, 123.25, 122.75, 122.51, 115.22, 60.36, 57.07, 40.94

Sources & evidence

ORD record
ord-1c0b3a6eb33646b28259a61165161718
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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