3-(Trifluoromethyl)phenyl isocyanate → HCID 52951735, compound

HRID 508608Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:14]1([C:20]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:23]=[C:22](NC(NC3C=CC=C(C(F)(F)F)C=3)=O)[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([C:20]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:23]=[C:22]([CH2:3][CH2:4][CH2:5][NH:9][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=3)=[O:11])[CH:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanate

HCID 52951272HCID 52951272, compound

Product 1

HCID 52951735HCID 52951735, compoundYield 84%

Procedure

The titled compound was prepared in 84% yield from 3-(trifluoromethyl)phenyl isocyanate using the procedure detailed for compound 7. mp 175.5-176.4° C. 1H NMR (300 MHz, DMSO-d6): δ 8.85 (s, 1H), 7.98 (s, 1H), 7.79 (d, J=9 Hz, 2H), 7.53-7.35 (m, 9H), 7.29-7.18 (m, 3H), 6.57 (s, 1H), 6.38 (t, J=6 Hz, 1H), 3.25-3.17 (m, 2H), 2.69 (t, J=8 Hz, 2H), 1.94-1.80 (m, 2H). MS (ESI) m/z: 544.16 (M+H+). Anal. Calcd for C26H24F3N5O3S: C, 57.45; H, 4.45; N, 12.88. Found: C, 57.31; H, 4.46; N, 12.74.

Sources & evidence

ORD record: ord-ba30f5b565534331828976c6c47f6212
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096532B2

Reaction notes

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