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

HRID 1076836Notes

Reaction equation

HRID 1076836 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:39])(=[O:38])[CH2:28][C:29]([CH2:34][C:35]([OH:37])=[O:36])([C:31]([OH:33])=[O:32])[OH:30]>C(O)C>[C:27]([OH:39])(=[O:38])[CH2:28][C:29]([CH2:34][C:35]([OH:37])=[O:36])([C:31]([OH:33])=[O:32])[OH:30].[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

4

Reactant 2

HCID 311Citric AcidHCID 38054Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

Product 1

HCID 867334385-Methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole citrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A hot solution of 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole (0.738 g.) in ethanol (45 ml.) is treated with a hot solution of citric acid (0.384 g.) in ethanol (2.5 ml.). The solution is allowed to cool to room temperature and then kept at 0° - 10°C. overnight. The precipitate which forms is collected by filtration, washed with ethanol and dried to give 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole citrate, m.p. 155° - 156°C. (dec.) with previous softening. Elemental analysis satisfactory for C26H31N3O9S.

Workup

  1. filtrationThe precipitate which forms is collected by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-65b1f206c2d0486ebe42e5141e51de1d
Source dataset
uspto-grants-1976_05
Patent number
US03957999

Reaction notes

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