Hydrochloric Acid → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazolesulfonamide

HRID 236235Notes

Reaction equation

HRID 236235 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:5](=[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)[N:18]=1.N12CCCCC1C=NCCC2.Cl>C(#N)C.O>[CH3:24][O:23][C:21]1[CH:22]=[C:17]([O:16][CH3:15])[N:18]=[C:19]([NH:25][C:26]([NH:14][S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=23)(=[O:13])=[O:12])=[O:27])[N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 138244262-Methyl-4-benzothiazolesulfonamide

Product 1

HCID 13824428N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazolesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 0.23 g of the product from Example 2 and 0.28 g of 4,6-dimethoxypyrimidin-2-ylcarbamic acid, phenyl ester in 5 mL of dry acetonitrile was treated at room temperature with 0.15 mL of 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU), added over a period of about one minute. The reaction solution was stirred at room temperature for 1.5 hour and was then diluted with 2 mL of water and acidified by the addition of 5% aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed well with water and ether, and dried. The yield of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methyl-4-benzothiazolesulfonamide was 0.21 g as a white powder, m.p. 187°-194° C. NMR (CDCl3 /DMSO-d6): δ 2.7 (3H, s), 4.05 (6H, s), 5.8 (1H, s), 7.5 (1H, t, J=8 Hz), 8.15 (1H, dd, J=2,8 Hz), 8.25 (1H, dd, J=2.8 Hz), 8.7 (1H, br s), 13.3 (1H, br s); IR(KBr): 3330, 1830, 1610, 1350, 1160 cm-1.

Workup

  1. additionadded over a period of about one minute
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed well with water and ether
  4. customdried

Sources & evidence

ORD record
ord-5d58501b036b4cfabc46d279944f4843
Source dataset
uspto-grants-1987_02
Patent number
US04643759

Reaction notes

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