Potassium Bromide → HCID 9925962, compound

HRID 1977107Notes

Reaction equation

HRID 1977107 reaction equation
[C:1]([CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[NH:17][C:18](=O)[CH3:19])(=[O:6])=[O:5])#[N:2].[K+].[Br-]>CO>[CH3:19][C:18]1[NH:17][C:8]2[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=2[S:4](=[O:6])(=[O:5])[C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 253877Potassium BromideHCID 21997646HCID 21997646, compound

Product 1

HCID 9925962HCID 9925962, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by base catalyzed ring closure of N-(2-cyanomethylsulfonyl-5-trifluoromethylphenyl)-acetamide by a procedure analogous to the procedure described in EXAMPLE 1 c); white flakes (from methanol), mp 329-333° C., 1H-NMR(CD3OD) δ (ppm): 8.20-8.10 (br d, 1H), 7.78-7.62 (m, 2H), 4.88 (br, H2O+NH), 2.52 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 156.4, 135.6, 133.1 (q, J=33 Hz), 126.6, 124.2, 123.0 (CF3, J=273 Hz), 121.9 (J=3.4 Hz), 116.2 (J=4.5 Hz), 112.4 (C≡N), 86.3 20.4; IR (KBr) ν (cm−1): 3301, 3195, 3133, 2214(C≡N), 1628, 1614, 1592, 1554, 1487, 1422, 1339, 1308, 1265, 1241, 1187, 1159, 1131, 1083, 890; MS m/e (rel. intensity): 288 (74%, M+), 224 (74%), 223 (100%), 203 (8%), 155 (9%), 69 (16%).

Sources & evidence

ORD record
ord-b3ade8d49b7b4ef59235ce5b61ad4755
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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