Tetrahydrofuran → 2-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][O:8][C:7]3[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:6]=3[C:5]=2[N:16]=1.O1CCCC1.[Br:22][C:23]([CH3:30])([CH3:29])[C:24]([N:26]=[C:27]=[O:28])=[O:25]>>[Br:22][C:23]([CH3:30])([CH3:29])[C:24]([NH:26][C:27](=[O:28])[NH:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][O:8][C:7]3[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:6]=3[C:5]=2[N:16]=1)=[O:25]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 579002668-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-ylamine

HCID 866523302-Bromo-2-methylpropanoyl isocyanate

Product 1

HCID 582038232-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide

Procedure

A mixture of 1250 mg (4.20 mmol) of 2-amino-8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine in tetrahydrofuran (6.75 mL, 83.2 mmol) was mixed with 1.25 g (6.00 mmol, 1.42 eq.) of crude 2-bromo-2-methylpropanoyl isocyanate and stirred for 20 hours. The precipitate was filtered off, washed with ethyl ether and dried on air to give 2-Bromo-2-methyl-N-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)carbamoylpropanamide. Weight 2.21 g (75%). MS(ESI+): 488.0