Hydrochloric Acid → Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate

HRID 354653Notes

Reaction equation

HRID 354653 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:33][O:34][CH:35]([CH3:37])[CH3:36])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1.CN(C)C=O.Cl>C(N(CC)CC)C.C(Cl)Cl>[C:1]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:33][O:34][CH:35]([CH3:36])[CH3:37])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 54000557Ethyl 2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)acetate

Product 1

HCID 54071115Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetateYield 129.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

13.2 g of trityl chloride were slowly added to a cooled mixture of 11 g of the product of Step C, 20 ml of dry dimethylformamide, 40 ml of methylene chloride and 6.2 ml of triethylamine and the mixture was stirred for 21/2 hours. 43 ml of N hydrochloric acid were added thereto and the mixture was stirred and decanted. The organic phase was washed with 40 ml of water and was extracted with methylene chloride. The extracts were dried and vacuum filtered. The filtrate was evaporated to dryness to obtain 27.7 g of ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate in the syn configuration.

Workup

  1. stirringthe mixture was stirred
  2. customdecanted
  3. washThe organic phase was washed with 40 ml of water
  4. extractionwas extracted with methylene chloride
  5. customThe extracts were dried
  6. filtrationvacuum filtered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-e2fdd840b414499e94d3acdc9081258a
Source dataset
uspto-grants-1983_03
Patent number
US04376203

Reaction notes

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