Methyl chloroformate → Tioxidazole

HRID 838988Notes

Reaction equation

HRID 838988 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:6]=2[N:7]=1.Cl[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[CH3:20][O:19][C:17](=[O:18])[NH:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 13556109HCID 13556109, compound

Product 1

HCID 72157Tioxidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 24.45 g. of 2-amino-6-n-propyloxybenzothiazole-hydrochloride in 100 ml of pyridine maintained at 0° C by an ice bath, is slowly added 9.45 g. of methyl chloroformate. After the addition is completed the mixture is allowed to warm up to room temperature. It is then poured on 300 g. of ice water. A solid is formed which is isolated by filtration and crystallized from ethanol to yield 20 g., m.p. 178°-180° C.

Workup

  1. additionAfter the addition
  2. additionIt is then poured on 300 g
  3. customA solid is formed which
  4. customis isolated by filtration
  5. customcrystallized from ethanol
  6. customto yield 20 g

Sources & evidence

ORD record
ord-5229637169a94a3cb5a661507c8234cb
Source dataset
uspto-grants-1978_06
Patent number
US04093731

Reaction notes

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