Isopropylamine → 6-bromo-N-isopropylbenzo[d]thiazol-2-amine

HRID 2077603Notes

Reaction equation

HRID 2077603 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](Cl)[S:8][C:4]=2[CH:3]=1.[CH3:12][CH:13]([NH2:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:15][CH:13]([CH3:14])[CH3:12])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 20498716-Bromo-2-chlorobenzothiazole

Product 1

HCID 772315096-bromo-N-isopropylbenzo[d]thiazol-2-amineYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A microwave reaction vial was charged with 6-bromo-2-chlorobenzo[d]thiazole (300 mg, 1.21 mmol), propan-2-amine (75 mg, 1.27 mmol), triethylamine (183 mg, 1.81 mmol) and 2.4 mL DMF. The vial was sealed, and the mixture was irradiated in the microwave for 20 min at 150° C. The reaction mixture was concentrated twice from toluene and purified by silica gel chromatography (0-50% 90/10 CH2Cl2/MeOH in CH2Cl2), which provided 6-bromo-N-isopropylbenzo[d]thiazol-2-amine (210 mg, 64%) as a white solid. MS (ESI pos. ion) m/z calc'd for C10H11BrN2S: 271.2/273.2. found 271.0/273.0.

Workup

  1. customA microwave reaction
  2. customThe vial was sealed
  3. customthe mixture was irradiated in the microwave for 20 min at 150° C
  4. concentrationThe reaction mixture was concentrated twice from toluene
  5. custompurified by silica gel chromatography (0-50% 90/10 CH2Cl2/MeOH in CH2Cl2), which

Sources & evidence

ORD record
ord-107cb63ac376477090ebfc17cd677973
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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