1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18354634, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:19]([OH:21])=O)[CH:16]=[CH:17][CH:18]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC2N(O)N=[N:28]C=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:19]([NH2:28])=[O:21])[CH:16]=[CH:17][CH:18]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
To a solution of 2-(4-nitrophenyl)benzo[d]oxazole-4-carboxylic acid (1.42 g, 5 mmol) in DMF (70 mL) was added HOBt (0.75 g, 5.5 mmol), NH4Cl (0.27 g, 5.0 mmol), DIPEA (1.94 g, 15.0 mmol) and EDCI (1.15 g, 6.0 mmol). The mixture was stirred at 30° C. for 18 hr. The resulting mixture was purged in water (10 mL) and aqueous hydrochloric acid (1 N) to pH=3, then filtered, and the filtrate was washed with saturated sodium bicarbonate solution (100 mL×2) and brine (100 mL×2), and dried in vacuum to obtain the crude product. Re-crystallization in THF obtained 2-(4-nitrophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (800 mg, yield 56%). LC-MS (ESI) m/e 284 [M+1]+.
Workup
- customThe resulting mixture was purged in water (10 mL)
- filtrationaqueous hydrochloric acid (1 N) to pH=3, then filtered
- washthe filtrate was washed with saturated sodium bicarbonate solution (100 mL×2) and brine (100 mL×2)
- customdried in vacuum
- customto obtain the crude product
Sources & evidence
- ORD record
- ord-eb044e4904fe407abd1cbc0922d7e84b
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088760B2
Reaction notes
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