4-Chlorophenyl Isocyanate → HCID 52951866, compound

HRID 508612Notes

Reaction equation

HRID 508612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[C:11]1([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[N:20]=[C:19](NC(NC3C=CC=C(C(F)(F)F)C=3)=O)[CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:8][CH2:5][CH2:4][CH2:3][C:19]2[CH:18]=[C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:21]([C:22]3[CH:23]=[CH:24][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:26][CH:27]=3)[N:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 52951272HCID 52951272, compound

Product 1

HCID 52951866HCID 52951866, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The titled compound was prepared in 92% yield from 4-chlorophenyl isocyanate using the procedure detailed for compound 7. mp 103.2-110.4° C. 1H NMR (300 MHz, DMSO-d6): δ 8.60 (s, 1H), 7.79 (d, J=9 Hz, 2H), 7.47-7.35 (m, 9H), 7.29-7.21 (m, 4H), 6.57 (s, 1H), 6.29 (t, J=6 Hz, 1H), 3.26-3.13 (m, 2H), 2.68 (t, J=8 Hz, 2H), 1.92-1.77 (m, 2H). MS (ESI) m/z: 510.14 (M+H+). Anal. Calcd for C25H24ClN5O3S.MeOH: C, 58.22; H, 4.98; N, 13.31. Found: C, 58.18; H, 4.78; N, 13.25.

Sources & evidence

ORD record
ord-881693bddb8e46c6802781b8e274405c
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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