Succinic Acid → 5-Methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole succinate

HRID 1076837Notes

Reaction equation

HRID 1076837 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:26]=1.[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31]>C(O)C.CCOCC>[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:17]=3)=[N:8][C:7]=2[CH:26]=1

Participants

5

Reactant 2

HCID 1110Succinic AcidHCID 38054Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

Product 1

HCID 215385975-Methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole succinate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole (0.738 g.) in ethanol (30 ml.) is treated at room temperature with a solution of succinic acid (0.236 g.) in ethanol 3.5 ml.). After 1 hour the solution is diluted with ether (70 ml.) and then kept at 0° - 10°C. overnight. The resulting precipitate is collected by filtration and dried to give 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole succinate, m.p. 150° - 153°C. Elemental analysis satisfactory for C24H29N3O6S.

Workup

  1. filtrationThe resulting precipitate is collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-ab487f54955646c385305d372c4e116b
Source dataset
uspto-grants-1976_05
Patent number
US03957999

Reaction notes

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