HCID 21883557, compound → HCID 21883547, compound

HRID 722372Notes

Reaction equation

[Cl:1][C:2]1[C:3]([S:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH:29]OS([O-])=O.[K+]>>[Cl:1][C:2]1[C:3]([S:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:29])=[CH:4][C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

Reactant 2

HCID 21883557HCID 21883557, compound

HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21883547HCID 21883547, compound

Procedure

Following a procedure similar to that described in Example 128, ethyl 6-chloro-7-[(4-chlorophenyl)thio]-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (Example 192) was treated with OXONE® yielding the products labeled Example 193 and Example 194: mp 213.8–217.4° C. 1H NMR (acetone-d6/300 MHz) 7.91 (s, 1H), 7.83 (d, 2H, J=8.7 Hz), 7.62 (m, 4H), 5.98 (q, 1H, J=6.8 Hz). 19F NMR (acetone-d6/282 MHz) −79.3 (d, J=7.2 Hz). ESLRMS m/z 435 (M−H). ESHRMS m/z 434.9470 (M−H, Calc'd 434.9472). Anal. Calc'd for C17H9Cl2F3O4S: C, 46.70; H, 2.07; Cl, 16.22; S, 7.33. Found: C, 46.80; H, 2.28; Cl, 16.75; S, 7.39.

Workup

customyielding the products

Sources & evidence

ORD record: ord-5c7af4acda8a451ca59663dc735d1f33
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138411B2

Reaction notes

Loading…