Hydrochloric Acid → 1-(7-Acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 712287Notes

Reaction equation

HRID 712287 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:24]([O:26]CC)=[CH2:25])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[C:24]([C:11]1[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866639991-[5-Benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

Product 1

HCID 866640001-(7-Acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-ureaYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[5-benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea was dissolved in THF (24 mL) and 2M aqueous hydrochloric acid (2 mL) was added and the reaction stirred at ambient temperature for 4 h, after which time LCMS indicated clean conversion to the ketone. The reaction solvent was removed in vacuo to give the desired compound (650 mg, 70% yield).

Workup

  1. customThe reaction solvent was removed in vacuo

Sources & evidence

ORD record
ord-463acb90b90b49829de631c4dafa9994
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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