Sodium Hydroxide → HCID 16058801, compound

HRID 1639551Notes

Reaction equation

HRID 1639551 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:11])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[S:33](Cl)(=[O:35])=[O:34]>>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[S:33]([O:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[S:8][C:4]=2[CH:3]=1)(=[O:35])=[O:34]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 5221832,6-Dichlorobenzenesulfonylchloride2×HCID 86622285HCID 86622285, compound

Product 1

HCID 16058801HCID 16058801, compound

Conditions

Temperature
20 °C

Procedure

To a solution of 260 mg of 1-(6-hydroxy-1,3-benzothiazol-2-yl)-3-(2-morpholin-4-ylethyl)urea in 19.4 cm3 of aqueous 0.1N sodium hydroxide solution are added 209 mg of finely ground 2,6-dichlorobenzenesulfonyl chloride. After stirring for about 5 hours at a temperature in the region of 20° C., a further 70 mg of 2,6-dichlorobenzenesulfonyl chloride are added. After stirring for about 18 hours at the same temperature, the reaction mixture is concentrated under reduced pressure (13 kPa) to a volume of about 5 cm3. The suspension obtained is cooled for about one hour at a temperature in the region of 5° C. The solid is filtered off by suction, washed with three times 2 cm3 of water precooled to about 5° C., and dried under reduced pressure (13 kPa) over phosphorus pentoxide. 216 mg of 2-{[(2-morpholin-4-ylethyl)carbamoyl]amino}-1,3-benzothiazol-6-yl 2,6-dichlorobenzenesulfonate are thus obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

  1. stirringAfter stirring for about 18 hours at the same temperature
  2. concentrationthe reaction mixture is concentrated under reduced pressure (13 kPa) to a volume of about 5 cm3
  3. customThe suspension obtained
  4. temperatureis cooled for about one hour at a temperature in the region of 5° C
  5. filtrationThe solid is filtered off by suction
  6. washwashed with three times 2 cm3 of water
  7. customprecooled to about 5° C.
  8. dry with materialdried under reduced pressure (13 kPa) over phosphorus pentoxide

Sources & evidence

ORD record
ord-c1b42ff77b774a2e9fd1f202625f6e05
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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