Trifluoroacetic acid → HCID 21938226, compound

HRID 2187759Notes

Reaction equation

HRID 2187759 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([S:28][CH3:29])=[CH:22]2)=[O:18].[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH:33]=O>C(Cl)Cl>[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH2:33][C:22]1[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([C:17]([O:16][CH3:15])=[O:18])[CH:20]=2)[NH:24][C:23]=1[S:28][CH3:29]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 134042,4-DichlorobenzaldehydeHCID 21938349HCID 21938349, compound

Product 1

HCID 21938226HCID 21938226, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a methylene chloride (10 ml) solution of trifluoroacetic acid (1.238 g) and triethylsilane (2.52 g), added is a methylene chloride (10 ml) solution of 5-methoxycarbonyl-2-methylthioindole (0.800 g), which had been prepared according to the method described in “Tetrahedron, 42 (16), 4511 (1986)”, and 2,4-dichlorobenzaldehyde (0.760 g), in an ice-water bath. This is stirred for 3 hours in the ice-water bath. The crystal formed is taken out through filtration and dried to obtain 3-(2,4-dichlorobenzyl)-5-methoxycarbonyl-2-methylthioindole (152) (0.727 g).

Workup

  1. customhad been prepared
  2. customThe crystal formed
  3. filtrationis taken out through filtration
  4. customdried

Sources & evidence

ORD record
ord-3177708fb23e45e8aae7af14036ffdb5
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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