Triethylamine → HCID 15457459, compound

HRID 1289064Notes

Reaction equation

HRID 1289064 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): δ6.8-7.4 (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-e8f4c80457c743b2a3f77af6dfa8a317
Source dataset
uspto-grants-1998_05
Patent number
US05747516

Reaction notes

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