Water → 2-Tert-butyl-5-chloro-6-nitrobenzothiazole

HRID 2118744Notes

Reaction equation

HRID 2118744 reaction equation
[C:1]([C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=1Cl)=[S:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O>CS(C)=O>[C:1]([C:5]1[S:6][C:9]2[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[C:12]([Cl:14])=[CH:13][C:8]=2[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 54175336N-t-butylthiocarbonyl-2,5-dichloro-4-nitroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 94 g of N-tert-butylthiocarbonyl-2,5-dichloro-4-nitroaniline, described in Example 1, in 360 ml of dimethylsulphoxide and 160 ml of triethylamine is heated at 140° for 10 hours under nitrogen. The reaction mixture is cooled and poured into water. The solid obtained is filtered and washed with water and air-dried to yield 2-tert-butyl-5-chloro-6-nitrobenzothiazole, melting at 65°-69°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe solid obtained
  3. filtrationis filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-98e5a3c4e1654808bded758f6146c3b0
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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