HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Phosgene → HCID 11003433, compound

HRID 742092
Notes
Print preview

Reaction equation

HRID 742092 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[O:6]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CN=N1.[C:32](Cl)(Cl)=[O:33]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[N:1]1([C:32]([O:25][C:19]([CH3:26])([C:16]2[CH:17]=[CH:18][C:13]([O:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:14][CH:15]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:33])[CH:5]=[N:4][CH:3]=[N:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 92571H-1,2,4-TriazoleHCID 10859095Ethyl 2-(4-phenoxyphenyl)lactateHCID 178418936HCID 178418936, compound

Product 1

HCID 11003433HCID 11003433, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
103 °C

Procedure

A mixture of 6.9 g of 1,2,4-triazole, 100 mL of toluene, 14.3 g of ethyl 2-(4phenoxyphenyl)lactate, and 20 g of triethylamine was heated to 103° C. to dissolve the triazole and then cooled to -60° C. Phosgene (6.4 g) was added at 57°-60° C. over 2.5 h. After holding the reaction mixture at 59°-60° C. for 1.25 h, the reaction mixture was cooled to -5° C. Ice (100 g) was added, and the temperature dropped to -8° C. The aqueous layer was separated and extracted one time with 15 mL of toluene. The organic layers were combined and washed with cold water (2 times with 25 mL), dried (MgSO4), filtered, and evaporated in vacuo to yield 19.6 g of the title compound as a viscous oil. 1H NMR (300 MHz, CDCl3): δ8.85 (s, 1H), 8.08 (s,1H), 7.59-7.00 (m, 11H), 4.25 (m,2H), 2.18 (s,3H), 1.23 (t,3H).

Workup

  1. temperaturecooled to -60° C
  2. customat 59°-60° C.
  3. customfor 1.25 h
  4. temperaturethe reaction mixture was cooled to -5° C
  5. additionthe temperature dropped to -8° C
  6. customThe aqueous layer was separated
  7. extractionextracted one time with 15 mL of toluene
  8. washwashed with cold water (2 times with 25 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-a71173dd1f1f4e23b635a9b145ddd388
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05552554

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes