Chlorosuccinimide → 4-Chloro-2-methylbenzo[d]thiazol-5-amine

HRID 970035Notes

Reaction equation

HRID 970035 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[Cl:12]N1C(=O)CCC1=O>C(O)(C)C>[Cl:12][C:11]1[C:6]2[N:7]=[C:8]([CH3:10])[S:9][C:5]=2[CH:4]=[CH:3][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 362295-Benzothiazolamine, 2-methyl-

Product 1

HCID 112178574-Chloro-2-methylbenzo[d]thiazol-5-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-amino-2-methylbenzothiazole (818 mg, 4.99 mmol) in isopropanol (12 mL) was added N-chlorosuccinimide (732 mg, 5.48 mmol). The mixture was stirred at 60° C. for 15 min., partitioned between DCM and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a residue that was purified with flash chromatography (EtOAc/DCM gradient elution). 4-Chloro-2-methylbenzothiazol-5-ylamine was obtained as off-white crystalline solid (510 mg, 51%). mp 121-122° C. (lit. 124° C.); TLC single spot at Rf 0.51 (20% EtOAc/DCM); 1H NMR (270 MHz, DMSO): δ 7.61 (1H, d, J=8.6 Hz, ArH), 6.91 (1H, d, J=8.6 Hz, ArH), 5.49 (2H, s, NH2), 2.75 (3H, s, CH3); APCI-MS 199 (MH)+.

Workup

  1. custompartitioned between DCM and 5% sodium bicarbonate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a residue that
  6. customwas purified with flash chromatography (EtOAc/DCM gradient elution)

Sources & evidence

ORD record
ord-cc106b59f5a04d1892e6b401a20c623f
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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