Ethyl isocyanate → HCID 11703962, compound

HRID 2243583Notes

Reaction equation

[C:1]1([C:7]2[O:19][C:10]3=[N:11][CH:12]=[C:13]4[C:17]([NH2:18])=[N:16][NH:15][C:14]4=[C:9]3[C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>C1COCC1.CN(C)C1C=CN=CC=1>[C:1]1([C:7]2[O:19][C:10]3=[N:11][CH:12]=[C:13]4[C:17]([NH:18][C:29]([NH:28][CH2:26][CH3:27])=[O:30])=[N:16][NH:15][C:14]4=[C:9]3[C:8]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 11 (22 mg, 0.068 mmol, 1.0 equiv) in THF (2 mL) was added 4-(Dimethylamino)pyridine (1 mg, 0.008 mmol, 0.1 equiv) and ethyl isocyanate (53 μL, 0.675 mmol, 10.0 equiv). After heating at 50° C. for 2 hrs, the solvent was removed in vacuo. The resulting yellow residue was purified by silica gel chromatography (5% MeOH:CH2Cl2) to afford urea 12a. MS (MH+) 398.4; Calculated 397.2 for C23H19N5O2.

Workup

customthe solvent was removed in vacuo
customThe resulting yellow residue was purified by silica gel chromatography (5% MeOH:CH2Cl2)

Sources & evidence

ORD record: ord-a82c9878e76d4a6e93921a64cca851cc
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674907B2

Reaction notes

Loading…