Chloroacetic Acid → HCID 135554983, compound

HRID 703075Notes

Reaction equation

HRID 703075 reaction equation
[CH2:1]([C:3]1[NH:8][C:7](=[O:9])[C:6]([SH:10])=[C:5]([NH:11][CH3:12])[N:4]=1)[CH3:2].Cl[CH2:14][C:15]([OH:17])=O.O.[OH-].[Na+].Cl>>[CH2:1]([C:3]1[NH:8][C:7](=[O:9])[C:6]2[S:10][CH2:14][C:15](=[O:17])[N:11]([CH3:12])[C:5]=2[N:4]=1)[CH3:2]

Participants

6

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 136023078HCID 136023078, compound

Product 1

HCID 135554983HCID 135554983, compound

Procedure

2-Ethyl-5-mercapto-6-methylamino-3H-pyrimidin-4-one (6.6g, 0.036 mole) from Example 112 and 3.37g (0.036 mole) of chloroacetic acid were added to approximately 120ml of water containing 4.27g (0.107 mole) of sodium hydroxide. The resultant solution was refluxed for approximately 4 hours, allowed to cool and acidified to about pH 2 with concentrated hydrochloric acid. The white solid was separated by filtration and dried (7.4g), then refluxed in approximately 100ml of acetic anhydride for about 2 hours and allowed to cool. The precipitate was removed by suction filtration, washed with diethyl ether and dried, providing 6.26g (78%) of 6,7-dihydro-2-ethyl-8-methyl-3H-pyrimido[5,4-b][1,4]thiazane-4,7-dione. The structural assignment was confirmed by infrared spectral analysis.

Workup

  1. temperatureto cool
  2. customThe white solid was separated by filtration
  3. customdried (7.4g)
  4. temperaturerefluxed in approximately 100ml of acetic anhydride for about 2 hours
  5. temperatureto cool
  6. customThe precipitate was removed by suction filtration
  7. washwashed with diethyl ether
  8. customdried
  9. customproviding 6.26g (78%) of 6,7-dihydro-2-ethyl-8-methyl-3H-pyrimido[5,4-b][1,4]thiazane-4,7-dione

Sources & evidence

ORD record
ord-3fa9517f3bb64d429e38975f3418e688
Source dataset
uspto-grants-1991_01
Patent number
US04981850

Reaction notes

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