4-Bromo-2-methylphenyl isocyanate → tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-[N-(2-methyl-4-bromophenyl)carbamoyloxy]-2(1H)-pyrimidinone

HRID 972402Notes

Reaction equation

HRID 972402 reaction equation
[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([OH:15])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3].[CH3:20][C:21]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[O:30]>C(N(CC)CC)C>[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([O:15][C:29](=[O:30])[NH:28][C:22]3[CH:23]=[CH:24][C:25]([Br:27])=[CH:26][C:21]=3[CH3:20])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 27355944-Bromo-2-methylphenyl isocyanateHCID 21400073tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21404013tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-[N-(2-methyl-4-bromophenyl)carbamoyloxy]-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

Tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole) and 2-methyl-4-bromophenyl isocyanate (3.5 ml; 0.06 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer. The mixture is stirred and triethylamine (1 drop) is added thereto. After the addition is completed the reaction mixture is allowed to stand for a period of about 1 hour. The mixture is then washed with hexane and is dried to yield the desired product tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-[N-(2-methyl-4-bromophenyl)carbamoyloxy]-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition
  3. washThe mixture is then washed with hexane
  4. customis dried

Sources & evidence

ORD record
ord-7cb6c9e219a74cd5aed59dbc0d5daeb3
Source dataset
uspto-grants-1977_10
Patent number
US04053298

Reaction notes

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