Water → HCID 19848014, compound

HRID 2351089Notes

Reaction equation

HRID 2351089 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][CH2:4][N:3]1[NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ClS([N:23]=[C:24]=[O:25])(=O)=O.O>C(OCC)(=O)C>[O:1]=[C:2]1[N:3]([NH:8][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:18])[CH2:4][CH2:5][CH2:6][N:7]1[C:24]([NH2:23])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 54188774(Tetrahydro-2-oxo-1(2H)-pyrimidinyl)carbamic acid, phenylmethyl ester

Product 1

HCID 19848014HCID 19848014, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (tetrahydro-2-oxo-1(2H)-pyrimidinyl)carbamic acid, phenylmethyl ester (35.5 g, 135.9 mmol) in 500 ml ethyl acetate, chlorosulfonyl isocyanate (24.0 g, 169.9 mmol) was added. The resulting solution was stirred for one hour and hydrolyzed by adding 175 ml water. The phases were separated, the organic phase washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent and trituration of the residue with ether yielded 38.0 g of the desired product, melting point 135.6° C.

Workup

  1. additionwas added
  2. customThe phases were separated
  3. washthe organic phase washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent and trituration of the residue with ether

Sources & evidence

ORD record
ord-af2c0a3830d342dc9ac29171caab9c1d
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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