Hexamethylphosphoramide → 2-tert-butyl-5-[N,N-dimethyl]amino-6-nitrobenzothiazole

HRID 2118756Notes

Reaction equation

HRID 2118756 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11](Cl)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH3:28])P(=O)(N(C)C)N(C)C>>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([N:19]([CH3:28])[CH3:18])=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 12679HexamethylphosphoramideHCID 197942022-Tert-butyl-5-chloro-6-nitrobenzothiazole

Product 1

HCID 201929392-tert-butyl-5-[N,N-dimethyl]amino-6-nitrobenzothiazole

Procedure

A solution of 16.2 g of 2-tert-butyl-5-chloro-6-nitrobenzothiazole, described in Example 5, in 150 ml hexamethyl phosphoric triamide is heated at 200° for 10 hours and poured into ice-water. The liquid separated is extracted with ether, dried over anhydrous sodium sulphate and the ether is evaporated under reduced pressure to give a red oil which is purified by silica gel column chromatography. Elution with benzene hexane (1:1) gives 2-tert-butyl-5-[N,N-dimethyl]amino-6-nitrobenzothiazole, melting at 65°-68°.

Workup

  1. temperatureis heated at 200° for 10 hours
  2. customThe liquid separated
  3. extractionis extracted with ether
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe ether is evaporated under reduced pressure
  6. customto give a red oil which
  7. customis purified by silica gel column chromatography
  8. washElution with benzene hexane (1:1)

Sources & evidence

ORD record
ord-b4f786bd61c548448186e6847e71f97a
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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