2-Bromoethyl chloroformate → HCID 86634651, compound

HRID 658089Notes

Reaction equation

HRID 658089 reaction equation
[SH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][C:7](=[O:10])[CH2:8][NH2:9])=[O:5].Cl[C:16]([O:18][CH2:19][CH2:20][Br:21])=[O:17]>CN(C)C(=O)C>[Br:21][CH2:20][CH2:19][O:18][C:16]([S:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][C:7](=[O:10])[CH2:8][NH2:9])=[O:5])=[O:17]

Participants

4

Reactant 2

HCID 785282-Bromoethyl chloroformateHCID 69048547HCID 69048547, compound

Product 1

HCID 86634651HCID 86634651, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(2-mercaptobenzoyl)glycinamide (1.05 g, 5.0 mmol) in N,N-dimethylacetamide (DMA, 25 ml) was added 2-bromoethyl chloroformate (1.22 g, 6.5 mmol). The reaction mixture was stirred for 8 h, the solvent was evaporated to dryness, and the residue was triturated with ethyl ether (25 ml. The resulting precipitate was filtered, washed with water and dried over CaCO2, Yield: 89%. 1H NMR (DMSO-d6): 3.71 (t, 1H, CH2), 3.78 (d, 2H, CH2), 3.86 (t, 1H, CH2), 4.45 (t, 1H, CH2), 4.51 (t, 1H, CH2), 7.11 (brs, 1H, NH2), 7.30 (brs, 1H, NH2), 7.36-7.58 (m, 5H, Ar—H, NH2), 8.26 (t, 2H, Py-H), 8.36 (t, 1H, NH), 8.52 (t, 1H, NH), 8.66 (t, 1H, Py-H), 9.12 (d, 21, Py-H).

Workup

  1. customthe solvent was evaporated to dryness
  2. customthe residue was triturated with ethyl ether (25 ml
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. dry with materialdried over CaCO2, Yield: 89%

Sources & evidence

ORD record
ord-92ee909dfba74c68b61c4c329f77a7f6
Source dataset
uspto-grants-2011_12
Patent number
US08076372B2

Reaction notes

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