Triethylamine → HCID 86664153, compound

HRID 1910689Notes

Reaction equation

HRID 1910689 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(N(CC)CC)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]3[CH2:13][CH2:14]3)[C:23](=[O:25])[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 94429TriphosgeneHCID 61609705HCID 61609705, compound

Product 1

HCID 86664153HCID 86664153, compoundYield 270.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-(cyclopropylamino)benzoic acid (4.70 g) and triethylamine (3.12 mL, 1 eq) in DCM (111 mL) was cooled to 0° C. and treated with triphosgene (2.31 g, 0.35 eq) in small portions. Dimethylaminopyridine (271 mg, 0.1 eq) was then added and the reaction was stirred at room temperature overnight. The crude was washed with cold 1 N HCl, and the organic portion was dried over sodium sulfate, and concentrated, then held under vacuum for 18 h delivering product (5.00 g, 95% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.88 (m, 2H), 7.68 (d, 1H), 2.90 (m, 1H), 1.16 (m, 2H), 0.80 (m, 2H). MS (ES+) m/z 260.0 (M+Na).

Workup

  1. washThe crude was washed with cold 1 N HCl
  2. dry with materialthe organic portion was dried over sodium sulfate
  3. concentrationconcentrated
  4. waitheld under vacuum for 18 h

Sources & evidence

ORD record
ord-973fbb22a2544829b211f789976d284f
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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