1,2-Dichloroethane → HCID 22250084, compound

HRID 889898Notes

Reaction equation

HRID 889898 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([OH:19])=O)=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12.[Cl:20]CCCl.CN(C)C=O.S(Cl)(Cl)=O>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[S:12][C:13]([C:17]([Cl:20])=[O:19])=[C:14]([CH3:16])[N:15]=3)[S:10][C:3]=12

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22250074HCID 22250074, compound

Product 1

HCID 22250084HCID 22250084, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4 g (12.9 mmol) of 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid 40 mL of 1,2-dichloroethane and 0.1 mL dimethyl formamide was carefully added 4.7 mL (64.4 mmol) of thionyl chloride. The reaction was heated to 90° C. for five hours. The reaction was cooled to room temperature and dry ethyl ether was added. The resulting brown precipitate was collected by vacuum filtration, washed with diethyl ether and dried to afford 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carbonyl chloride (3.31 g) in 78% yield. C12H6Cl2N2OS2: APCI m/z (in methanol to give methyl ester) 325.1/327.1 (pos.); 1H NMR (d6-DMSO): δ 8.68 (d, 1H, J=5.0 Hz), 8.32 (s, 1H), 8.65 (d, 1H, J=5.0 Hz), 2.39 (s, 3H) ppm.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting brown precipitate was collected by vacuum filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-da6df010553b423e9e173a1befebaac2
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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