Dichloromethane → HCID 58941825, compound

HRID 2097640Notes

Reaction equation

HRID 2097640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[S:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:29](Cl)Cl.CCN(C(C)C)C(C)C.FC(F)(F)S(OC)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])[S:11][CH3:29])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 81531DiisopropylethylamineHCID 58941925HCID 58941925, compound

Product 1

HCID 58941825HCID 58941825, compound

Procedure

To a solution of N-(3-chloro-4-fluorophenyl)-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carbothioamide (0.18 g, 0.00039 mol) in anhydrous DCM (3 ml, 0.04 mol) under N2 was added DIPEA (82 μL, 0.00047 mol) followed by methyl trifluoromethanesulfonate (47 μL, 0.00043 mol). The reaction was stirred for 5 minutes and then concentrated in vacuo. The crude material was used in the next step. The product amount was estimated (185 mg, 100%). MF═C20H29ClFN3OS2Si; LCMS calculated for C20H30ClFN3OS2Si (M+H)+: m/z=474.1.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c11a077ca9e9430fa5dec3f375d8efe0
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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