Dichloromethane → HCID 58941891, compound

HRID 1845767Notes

Reaction equation

HRID 1845767 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-4c8b2e475bef441485142e9d4c704d83
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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