1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66621468, compound

HRID 415181Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=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.O>[N+:1]([C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 2-(3-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 17 hr. To the resulting mixture, water (10 mL) was added and 1N aqueous hydrochloric acid to pH=3, then filtered, the filtrate was washed with saturated sodium bicarbonate solution (100 mL×2), brine (100 mL×2) and dried in vacuum to get a crude product. The crude product was re-crystallized in THF to obtain 2-(3-nitrophenyl)benzo[d]oxazole-4-carboxamide as a yellow solid (700 mg, yield 49%); LC-MS (ESI) m/z 284 [M+1]−.

Workup

filtration1N aqueous hydrochloric acid to pH=3, then filtered
washthe filtrate was washed with saturated sodium bicarbonate solution (100 mL×2), brine (100 mL×2)
customdried in vacuum
customto get a crude product
customThe crude product was re-crystallized in THF

Sources & evidence

ORD record: ord-a8f8a4ea043748958603038039cd1c21
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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