Chloroacetone → HCID 20321411, compound

HRID 866476Notes

Reaction equation

HRID 866476 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:6])=[S:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25]([CH3:27])=[O:26]>CCOC(C)=O>[OH:26][C:25]1([CH3:27])[CH2:24][S:2][CH:1]=[N:3][CH:4]1[C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)=[O:6]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 20321422HCID 20321422, compound

Product 1

HCID 20321411HCID 20321411, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-methoxybenzyl N-thioformyl-glycinate (4.79 g., 20 mMols), anhydrous powdered K2CO3 (8.29 g., 60 mMols), Me2CO (50 ml.), and ClCH2COCH3 (2.0 ml., 25 mMols) is stirred in a capped flask at room temperature for 6.5 hrs. The mixture is diluted with EtOAc (100 ml.) and filtered. The filtrate is evaporated in vacuo to an oil which is taken up in Et2O, washed twice with H2O and brine, dried with MgSO4, filtered, and evaporated in vacuo to an orange semi-solid (5.36 g.). The crude product is dissolved in warm PhH (25 ml.) and the solution is left in a refrigerator. The pale yellow crystals of p-methoxybenzyl 5-hydroxy-5-methyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (2.23 g.) are collected, washed with cold PhH and petroleum ether, and dried in vacuo: mp 102°-103° C. (micro hot stage); ir (CHCl3) 2.97, 5.82, 6.21, 6.62, 7.97, 8.51, 9.62, and 12.04μ; nmr (CDCl3) δ1.35 (s, 3, CH3), 2.75 (d of d, l, J=12 Hz and J=1Hz, SCH), 3.07 (d, l, J=12Hz, SCH), 3,25 (br s, l, OH), 3.82 (s, 3, OCH3), 4.17 (d of d, l, J=2Hz and J=1Hz, H4), 5.18 (s, 2, CH2Ar), 6.87 and 7.33 (two d's 4, J=9Hz, ArH), and 8.23 (d, l, J=2Hz, H2); mass spectrum m/e 295 (M+), 222, 131, and 121.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated in vacuo to an oil which
  3. washwashed twice with H2O and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo to an orange semi-solid (5.36 g.)
  7. dissolutionThe crude product is dissolved in warm PhH (25 ml.)
  8. waitthe solution is left in a refrigerator
  9. customThe pale yellow crystals of p-methoxybenzyl 5-hydroxy-5-methyl-5,6-dihydro-4H-1,3-thiazine-4-carboxylate (2.23 g.) are collected
  10. washwashed with cold PhH and petroleum ether
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3dfd015c026a46bd9a655ad14d20e969
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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