4-(Trifluoromethyl)phenyl isocyanate → HCID 25252974, compound

HRID 2063459Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].[Cl:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[CH:24]=[N:23][N:22]=[C:21]2[C@H:25]2[CH2:29][CH2:28][CH2:27][NH:26]2)=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[CH:24]=[N:23][N:22]=[C:21]2[C@H:25]2[CH2:29][CH2:28][CH2:27][N:26]2[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=2)=[O:3])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 1-isocyanato-4-(trifluoromethyl)benzene (46.3 mg, 0.2474 mmol) in 8 mL of CH2Cl2 at 0° C. was slowly added a solution of (R)-4-(4-chlorobenzyl)-3-(pyrrolidin-2-yl)-4H-1,2,4-triazole (0.050 g, 0.1903 mmol) in dichloromethane (2 mL). The resulting mixture was stirred 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was concentrated in vacuo. Flash chromatography purification ((Hex/EtOAc with 10% of MeOH) afforded the desired product (68 mg, 79.4%).

Workup

customat room temperature
customovernight
concentrationThe reaction mixture was concentrated in vacuo
customFlash chromatography purification ((Hex/EtOAc with 10% of MeOH)

Sources & evidence

ORD record: ord-f78a8d0cf7234b4895cafabb909e3485
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288371B2

Reaction notes

Loading…