Sodium Hydroxide → HCID 11303260, compound

HRID 1884906Notes

Reaction equation

[OH-].[Na+].[Cl:3][S:4]([OH:7])(=O)=[O:5].[Cl:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[CH2:18][CH3:19])=[C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1>>[Cl:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[CH2:18][CH3:19])=[C:11]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([S:4]([Cl:3])(=[O:7])=[O:5])=[CH:23][CH:22]=2)[N:10]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 24638Chlorosulfonic acid

HCID 23504768HCID 23504768, compound

Product 1

HCID 11303260HCID 11303260, compoundYield 89.6%

Conditions

Temperature: 0 °C

Procedure

A three necked round bottomed flask of 250 ml equipped with a bubbler (NaOH) and a magnetic stirrer is charged with 32.2 ml of 98% chlorosulfonic acid (483 mmoles) and cooled to 0° C. 22 g of 2-chloro-9-ethyl-6-(phenyl-amino)-9H-purine (80 mmoles) are added slowly. The mixture is stirred at RT for 2 hours and at 60° C. for 1 hour. The crude mixture is then poured drop by drop into a water bath cooled to 0° C., filtered and dried at 50° C. under HV. 26.67 g (89% yield) of 2-chloro-6-(4-chlorosulfonyl-phenyl-amino)-9-ethyl-9H-purine are obtained as a white crystalline powder. Rf=0.52 (CH2Cl2/MeOH (95/5); m.p. decomp. 220° C.; ESI-MS: 372 (M+H)+; 1H-NMR (d6-DMSO, 200 MHz, TMS): 1.4 ppm (t, 3H, J1=7 Hz, H1), 4.2 ppm (q, 2H, J1=7 Hz, H2), 7.55 ppm (d, 2H, J2=9 Hz, H5), 7.75 ppm (d, 2H, J2=9 Hz, H6), 8.55 ppm (s, 1H, H3), 10.5 ppm (s, 1H, H4).

Workup

temperaturecooled to 0° C.
filtrationfiltered
customdried at 50° C. under HV

Sources & evidence

ORD record: ord-bb975469594c4d379cf7575cdf550e9e
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06767906B2

Reaction notes

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