Ethyl isocyanate → N-ethyl-2-(ethylcarbamoylamino)-5-methoxy-1,3-benzothiazole-7-carboxamide

HRID 712281Notes

Reaction equation

HRID 712281 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[S:8][C:9]2[C:15]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[CH:14][C:13]([O:21][CH3:22])=[CH:12][C:10]=2[N:11]=1>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCOCC1>[CH2:19]([NH:18][C:16]([C:15]1[C:9]2[S:8][C:7]([NH:6][C:4](=[O:5])[NH:3][CH2:1][CH3:2])=[N:11][C:10]=2[CH:12]=[C:13]([O:21][CH3:22])[CH:14]=1)=[O:17])[CH3:20]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 866639932-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamide

Product 1

HCID 86663994N-ethyl-2-(ethylcarbamoylamino)-5-methoxy-1,3-benzothiazole-7-carboxamide

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl isocyanate (0.87 mL, 10.9 mmol) was added to a suspension of 2-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamide (549 mg, 2.18 mmol) and dibutyl tin diacetate (4 drops, catalytic amount) in dioxane (12 mL). The reaction was heated to 60° C. for 8 hours after which time LCMS indicated clean conversion to the desired product. The reaction solvent was removed in vacuo and the crude material used directly in the next step.

Sources & evidence

ORD record
ord-a0e267211e0945af90b57580a3dae7ab
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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