4-Amino-1-butanol → Benzothiazole-6-carboxylic acid (4-hydroxy-butyl)-amide

HRID 1942348Notes

Reaction equation

HRID 1942348 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C1N=CN(C(N2C=NC=C2)=O)C=1>O1CCCC1>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]([C:7]1[CH:8]=[CH:9][C:4]2[N:3]=[CH:2][S:1][C:5]=2[CH:6]=1)=[O:12]

Participants

5

Reactant 3

HCID 258684-Amino-1-butanolHCID 682631,1'-CarbonyldiimidazoleHCID 601670Benzothiazole-6-carboxylic acid

Product 1

HCID 66937214Benzothiazole-6-carboxylic acid (4-hydroxy-butyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.69 g (15 mmol) of benzothiazole-6-carboxylic acid is dissolved in a mixture of 1.34 g (15 mmol) 4-amino-butan-1-ol and 70 mL dry tetrahydrofuran. 2.43 g (15 mmol) of CDI is added after stirring for 30 minutes and then stirred for another hour. The mixture is concentrated in vacuum. The resulting residue is suspended in dichloromethane, water is added, and the organic phase is separated. The aqueous phase is extracted with dichloromethane twice. The combined organic phases are dried over sodium sulfate and concentrated in vacuum.

Workup

  1. stirringstirred for another hour
  2. concentrationThe mixture is concentrated in vacuum
  3. additionwater is added
  4. customthe organic phase is separated
  5. extractionThe aqueous phase is extracted with dichloromethane twice
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-21ab8c46101e43358f6759be11f8245b
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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