Water → Ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetate

HRID 1462034Notes

Reaction equation

HRID 1462034 reaction equation
[OH:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5].CI.[C:36]([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:36][O:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate

Product 1

HCID 6005279Ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetateYield 100.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ethyl (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetate (II) (5.00 g, 10.9 mmoles), CH3I (2.04 mL, 32.8 mmoles) and K2CO3 (4.54 g, 32.8 mmoles) in dry dimethylsulfoxide (DMSO) (100 mL) was stirred at room temperature overnight and then poured into water (250 mL). The precipitate which formed was collected by filtration, washed with water and dried to give the title compound (5.15 g, quantitative yield). M.p. 115° C. (dec.).

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-24a8def15120407e8189113bc3f853d1
Source dataset
uspto-grants-1984_07
Patent number
US04457929

Reaction notes

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