Tert-Butylamine → N-(1,1-Dimethylethyl)-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinesulfonamide

HRID 2072780Notes

Reaction equation

HRID 2072780 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([S:8](Cl)(=[O:10])=[O:9])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[CH3:1][N:2]1[CH:7]=[C:6]([S:8]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:10])=[O:9])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

4

Reactant 2

HCID 6385Tert-Butylamine2×HCID 49627171,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride

Product 1

HCID 19860385N-(1,1-Dimethylethyl)-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1,3-dimethyl-2,4-dioxo-5-pyrimidinesulfonyl chloride (300 g, 1.26M) in methylene chloride (2500 mL) at room temperature was added dropwise tert-butylamine (300 mL, 2.85M). The exotherm was allowed to proceed to 35° C. with mild cooling. After addition the reaction was refluxed for 30 minutes, cooled to room temperature and the tert-butylamine.HCl filtered off. The methylene chloride was then washed with diluted hydrochloric acid (700 mL), dried over MgSO4, and stripped under vacuo. Recrystallization of the white solid from ethanol afforded the desired compound (652 g, 94%) in three crops, m.p. 143°-144° C.

Workup

  1. customto proceed to 35° C. with mild cooling
  2. additionAfter addition the reaction
  3. temperaturewas refluxed for 30 minutes
  4. filtrationHCl filtered off
  5. washThe methylene chloride was then washed with diluted hydrochloric acid (700 mL)
  6. dry with materialdried over MgSO4
  7. customRecrystallization of the white solid from ethanol

Sources & evidence

ORD record
ord-ea2d020625514c8f9e29cad7a8b6c201
Source dataset
uspto-grants-1990_04
Patent number
US04914203

Reaction notes

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