Benzoyl chloride → HCID 13670754, compound

HRID 476969Notes

Reaction equation

HRID 476969 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([N:11]([CH3:13])[CH3:12])[CH2:8][CH2:7][C:5]=2[N:6]=1.[C:14]([Cl:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[ClH:22].[ClH:22].[C:14]([NH:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([N:11]([CH3:13])[CH3:12])[CH2:8][CH2:7][C:5]=2[N:6]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 13670672HCID 13670672, compound

Product 1

HCID 13670754HCID 13670754, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.0 g (15 mMol) of 2-amino-6-dimethylamino-4,5,6,7-tetrahydro-benzthiazole are dissolved in 15 ml of pyridine and 2.1 g (15 mMol) of benzoylchloride are added dropwise. After standing overnight the mixture is concentrated, mixed with soda solution and extracted with chloroform. The chloroform extract is concentrated and then chromatographed on silica gel (eluant: methylenechloride/methanol=9/1). The isolated base (melting point 174° C.) is dissolved in acetone and the dihydrochloride is precipitated with isopropanolic hydrochloric acid.

Workup

  1. concentrationthe mixture is concentrated
  2. additionmixed with soda solution
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. concentrationis concentrated
  6. customchromatographed on silica gel (eluant: methylenechloride/methanol=9/1)
  7. dissolutionThe isolated base (melting point 174° C.) is dissolved in acetone
  8. customthe dihydrochloride is precipitated with isopropanolic hydrochloric acid

Sources & evidence

ORD record
ord-ac78789785384d6bafc71085b05a42b7
Source dataset
uspto-grants-1989_12
Patent number
US04886812

Reaction notes

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