Oxalyl chloride → HCID 10801669, compound

HRID 394758Notes

Reaction equation

HRID 394758 reaction equation
[N+:1]([C:4]1[C:9]2[S:10](=O)[C:11]3[CH:16]=[N:15][CH:14]=[N:13][C:12]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:21])=O>CN(C=O)C.ClCCCl>[Cl:21][C:16]1[C:11]2[S:10][C:9]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 68468977HCID 68468977, compound

Product 1

HCID 10801669HCID 10801669, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

Dry DMF (5 drops) was added to a mixture of 6-nitrobenzothieno[3,2-d]pyrimidone (161 mg, 0.65 mmol) and oxalyl chloride (0.28 mL, 3.2 mmol) in 1,2-dichloroethane (5 mL). The reaction was heated at 85° C. for 7.5 hours then cooled to 25° C. The solid was Buchner filtered and washed with CH2Cl2 and air dried. 4-Chloro-6-nitrobenzothieno[3,2-d]pyrimidine was obtained as a gray solid (166 mg, 96% crude).

Workup

  1. temperaturethen cooled to 25° C
  2. filtrationfiltered
  3. washwashed with CH2Cl2 and air
  4. customdried

Sources & evidence

ORD record
ord-1c5ec4cc74c4410384e9c1f6559c2840
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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