Phosgene → 1055074-94-6

HRID 583789Notes

Reaction equation

HRID 583789 reaction equation
[CH3:1][O:2][C:3]1[S:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.C1(N(C)[CH:17]=[O:18])C=CC=CC=1.P(Cl)(Cl)(Cl)=O.C(Cl)(Cl)=O.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[S:4][C:5]([CH:17]=[O:18])=[C:6]([O:8][CH3:9])[N:7]=1

Participants

7

Reactant 5

HCID 6371PhosgeneHCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 67749Trifluoromethanesulfonic anhydrideHCID 22342547HCID 22342547, compound

Product 1

HCID 223425451055074-94-6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,4-dimethoxythiazole (0.01 mol), which may be prepared as described in Step (a) above, in dichloromethane is added N-phenyl-N-methylformamide (0.01 mol) and phosphorous oxychloride (POCl3, 0.01 mol), or optionally phosgene or trifluoromethanesulfonic acid anhydride instead of POCl3, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the mixture is partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 2,4-dimethoxythiazole-5-carboxaldehyde, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Workup

  1. customReaction progress

Sources & evidence

ORD record
ord-7d864eb5c8f44f6aaf3dec010a192b4f
Source dataset
uspto-grants-2005_08
Patent number
US06924276B2

Reaction notes

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