Thionyl Chloride → N-Benzyl-1,3-benzothiazol-2-amine

HRID 1414105Notes

Reaction equation

HRID 1414105 reaction equation
[CH2:1]([NH:8][C:9](=[S:17])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>O>[CH2:1]([NH:8][C:9]1[S:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6683001-Benzyl-3-phenyl-2-thiourea

Product 1

HCID 617555N-Benzyl-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

240.0 Parts of N'-benzyl-N-phenylthiourea are added, while stirring, over a period of 90 minutes to 334.6 parts of thionyl chloride of approximately 65° C. The reaction mixture is then refluxed (65° to 70° C.) for 5 hours while stirring. The cyclization melt obtained is hydrolyzed with 3,200 parts of water analogously to Example 53 and further treated as described in said Example. 221.5 Parts (92.3% of the theory) of 2-benzylamino-benzthiazole melting at 159° C. are obtained.

Workup

  1. temperatureThe reaction mixture is then refluxed (65° to 70° C.) for 5 hours
  2. customThe cyclization melt obtained
  3. additionfurther treated

Sources & evidence

ORD record
ord-6bdd0c91673542548f8f8ae839720fb0
Source dataset
uspto-grants-1981_02
Patent number
US04252963

Reaction notes

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