Dichloromethane → HCID 58941891, compound

HRID 2097638Notes

Reaction equation

HRID 2097638 reaction equation
[CH:1]([Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:5][CH2:6][C:7]1[S:11][N:10]=[N:9][C:8]=1[C:12]([O:14]C)=O)([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])[NH2:26].C(Cl)Cl.C[Al](C)C>CCCCCC>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:12]([C:8]2[N:9]=[N:10][S:11][C:7]=2[CH2:6][O:5][Si:4]([CH:16]([CH3:17])[CH3:18])([CH:19]([CH3:20])[CH3:21])[CH:1]([CH3:2])[CH3:3])=[O:14])[CH:27]=[CH:28][C:29]=1[F:30]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 97083-Chloro-4-fluoroanilineHCID 16682925TrimethylaluminumHCID 58941848HCID 58941848, compound

Product 1

HCID 58941891HCID 58941891, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a cooled solution (0° C.) of methyl 5-[(triisopropylsilyl)oxy]methyl-1,2,3-thiadiazole-4-carboxylate (2.2 g, 0.0066 mol) and 3-chloro-4-fluoroaniline (1.5 g, 0.010 mol) in DCM (20 mL, 0.4 mol) was added 2.0 M of trimethylaluminum in hexane (12 mL) under nitrogen and stirred for 15 minutes. The volatiles were removed in vacuo and the crude was purified by flash chromatography to give the desired product (2.3 g, 78%). MF═C19H27ClFN3O2SSi; LCMS calculated for C19H28ClFN3O2SSi (M+H)+: m/z=444.1.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-1afcc74759c841f5af0dcbbed4e83720
Source dataset
uspto-grants-2013_05
Patent number
US08450351B2

Reaction notes

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