Ammonia → HCID 46932238, compound

HRID 1192055Notes

Reaction equation

HRID 1192055 reaction equation
Br[CH:2]([C:4]1[S:8][C:7]([S:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=1)[CH3:3].[NH3:21]>CO>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[S:9][C:7]1[S:8][C:4]([CH:2]([NH2:21])[CH3:3])=[CH:5][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 60207313HCID 60207313, compound

Product 1

HCID 46932238HCID 46932238, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

5-(1-bromoethyl)-2-(2,4-dichlorophenyl)sulfanyl-3-nitro-thiophene (0.2 g, 0.49 mmol) was dissolved in ammonia in MeOH (2 M, 8 mL). The resulting mixture was sealed in a steel bomb and was heated at 100° C. for 2 hours. The reaction mixture was concentrated and the crude solid was purified by silica gel chromatography using a 98:2 mixture of dichloromethane and methanol as eluent to afford the title product (16 mg, 10% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.38 (1H, m), 8.08 (1H, m), 7.99 (1H, m), 7.82 (1H, s), 7.71 (1H, m), 4.61(1H, m), 1.45 (3H, d). MS m/z: 331.8 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude solid was purified by silica gel chromatography
  3. additiona 98:2 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-559e9843d4ae459e9be6b2ec126b03ff
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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