Triethylamine → HCID 15457459, compound

HRID 376841Notes

Reaction equation

HRID 376841 reaction equation
[CH3:1][N:2]([C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[NH2:3].[C:20](Cl)(Cl)=[S:21].C(N(CC)CC)C>O1CCCC1>[CH3:1][N:2]1[C:4](=[O:5])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[S:21])[NH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 19360031HCID 19360031, compound

Product 1

HCID 15457459HCID 15457459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.54 g of 1-methyl-N-(2-phenoxyphenyl)hydrazinecarboxamide in 50 mL of tetrahydrofuran, cooled in an ice bath, was treated with 0.46 mL of thiophosgene, and then 1.68 mL of triethylamine. A precipitate formed and the mixture was stirred at ambient temperature overnight. The precipitate was removed by filtration and washed with tetrahydrofuran. The combined filtrate and washings were concentrated under reduced pressure to afford 1.8 g of an amber glassy oil. The crude material was used in the next step without further purification. 1H NMR (CDCl3): δ 6.8-7.4 (m, 9H), 3.57 (s,3H).

Workup

  1. customA precipitate formed
  2. customThe precipitate was removed by filtration
  3. washwashed with tetrahydrofuran
  4. concentrationThe combined filtrate and washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-5466bda5c4ed41c1a087161739ea64c0
Source dataset
uspto-grants-2000_02
Patent number
US06022870

Reaction notes

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