Chloroacetonitrile → HCID 18924851, compound

HRID 1288818Notes

Reaction equation

HRID 1288818 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:20])=[C:5]([CH3:19])[C:6]=1[C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1.[Cl:21][CH2:22][C:23]#[N:24].[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:21][CH2:22][C:23]1[N:24]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)[C:6]2[C:5]([CH3:19])=[C:4]([CH3:20])[S:3][C:2]=2[N:1]=1

Participants

4

Reactant 3

HCID 7856ChloroacetonitrileHCID 858786HCID 858786, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18924851HCID 18924851, compoundYield 44%

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-3-(3,4-dimethoxybenzoyl)-4,5-dimethylthiophene (3.0 g) and chloroacetonitrile (11 g) was added, in limited amounts, powdered aluminum chloride (2.75 g). The mixture was stirred for 2.5 hours at 100° C. The reaction mixture was poured into ice-water, which was subjected to extraction with chloroform. The chloroform layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, which was dried (MgSO4). Chloroform was distilled off, and the residue was subjected to column chromatography on silica gel. From the fraction eluted with dichloromethane, 2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidine (1.58 g, 44%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p.117°-118° C.

Workup

  1. extractionwas subjected to extraction with chloroform
  2. washThe chloroform layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, which
  3. dry with materialwas dried (MgSO4)
  4. distillationChloroform was distilled off
  5. washFrom the fraction eluted with dichloromethane

Sources & evidence

ORD record
ord-f92f0e4344ae4a7da45f8915a22684c2
Source dataset
uspto-grants-1998_05
Patent number
US05747486

Reaction notes

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