Hydrochloric Acid → 5-Acetyl-N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-ethoxybenzenesulfonamide

HRID 2118449Notes

Reaction equation

HRID 2118449 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH3:16])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[N:20]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH3:16])=[C:8]([S:10]([NH:13][C:28]([NH:27][C:21]2[N:20]=[C:19]([O:18][CH3:17])[CH:24]=[C:23]([O:25][CH3:26])[N:22]=2)=[O:29])(=[O:11])=[O:12])[CH:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 13921459108356-41-8

Product 1

HCID 139214605-Acetyl-N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-ethoxybenzenesulfonamideYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 0.2 g of the compound from Example 8, 0.23 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 10 ml of dry acetonitrile was added 127 μl of DBU. After being stirred for 1 hr, the mixture was treated with 40 ml of water and 1N HCl in a dropwise manner until the pH was 3. The precipitate was filtered off and washed with water and ether/hexane (1/1), to give 0.27 g of a solid, m.p. 192°-193° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water and ether/hexane (1/1)

Sources & evidence

ORD record
ord-72a6853ce4b64fb6af532a49a215b817
Source dataset
uspto-grants-1987_07
Patent number
US04678498

Reaction notes

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