Water → 3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

HRID 587135

Reaction equation

HRID 587135 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH2:16][S:17]([NH2:20])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=1.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C:10]2[CH:11]=[C:12]([CH2:16][S:17]([NH2:20])(=[O:18])=[O:19])[CH:13]=[CH:14][CH:15]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 178102,4-Dichloro-1,3,5-triazineHCID 516892Sodium BicarbonateHCID 13266255(3-Aminophenyl)methanesulfonamide

Product 1

HCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dichloro-1,3,5-triazine (1.0 eq) in dry DMF (0.7 M) at 0° C. under N2 atmosphere was added a solution of (3-aminophenyl)-methanesulfonamide (1.0 eq) in dry DMF (0.7 M). The reaction mixture was stirred for 2.5 h at 0° C. Then water was added and the aqueous solution was neutralized with sat. aq. NaHCO3 solution. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4. Evaporation of solvent gave A1 as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, d6-DMSO, 300K) δ 4.26 (s, 2H), 6.89 (s, 2H), 7.15 (d, J=7.4 Hz, 1H), 7.36 (d, J=7.4 Hz, 1H), 7.66 (d, J=7.4 Hz, 1H), 8.64 (s, 1H), 9.75 (br. s, 1H), 10.83 (s, 1H). MS (ES) C10H10ClN5O2S requires: 299. found: 300 (M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-4c537d3662694d899423edc50d09fd9b
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Linked notes

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