Water → 4-{[Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amino]-methyl}-benzoic acid

HRID 1942397Notes

Reaction equation

C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:21][CH2:22][CH3:23])[CH:12]2[CH2:20][CH2:19][C:15]3[N:16]=[CH:17][S:18][C:14]=3[CH2:13]2)=[CH:6][CH:5]=1.[OH-].[Na+].O>C(O)(=O)C>[CH2:21]([N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:24])=[O:2])=[CH:9][CH:8]=1)[CH:12]1[CH2:20][CH2:19][C:15]2[N:16]=[CH:17][S:18][C:14]=2[CH2:13]1)[CH2:22][CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.93 g (5.6 mmol) 42A, 840 mg (21 mmol) sodium hydroxide and 25 mL water is stirred for 4 hours at 80° C. The mixture is allowed to cool to room temperature and then neutralized with acetic acid and extracted three times with dichloromethane. The combined organic fractions are dried with sodium sulfate, and the solvent is evaporated in vacuum.

Workup

temperatureto cool to room temperature
extractionextracted three times with dichloromethane
dry with materialThe combined organic fractions are dried with sodium sulfate
customthe solvent is evaporated in vacuum

Sources & evidence

ORD record: ord-7c877cc7518746599f23fd706423cb06
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389555B2

Reaction notes

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