Water → HCID 22045906, compound

HRID 1599811Notes

Reaction equation

HRID 1599811 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Br:11][CH2:12][C:13](Br)=[O:14].O>CN(C=O)C.O1CCOCC1>[Br:11][CH2:12][C:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 61147Bromoacetyl bromide

Product 1

HCID 22045906HCID 22045906, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-aminobenzoic acid (5.0 g, 0.036 mol) in anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) was cooled to 0° C. in a 250 mL 3-necked flask which was fitted with a constant additional funnel. Bromoacetyl bromide (7.36 g, 3.2 mL, 100 mol %) was added dropwise, keeping the internal temperature between 0° C. and 2° C. After the addition was completed (~30 min), the reaction mixture was stirred overnight at rt. Water (100 mL) was added, and then the light crystalline compound which precipitated was filtered, washed with 5% HBr, washed several times with water (200 mL), and then dried in a vacuum oven for 20 h at 40°-45° C., affording 9.3 g (99%) of the title compound: mp 245°-246.7° C.; 1H NMR (DMSO-d6) δ10.6 (s, 1H, NH), 7.91 (d, 2H, J=8.8), 7.69 (d, 2H, J=8.4), 4.10 (s, 2H); 13C NMR (DMSO-d6) δ168.88, 165.38, 142.62, 130.53, 125.78, 118.62, 30.30; MS (EI, m/z) 257 (M+), 258.9 (M+ 2+). HRMS (EI) calcd for C9H8NO3Br 256.9686, found 256.9677. Anal. Calcd. for C9H8NO3Br: C, 41.88; H, 3.12; N, 5.43. Found: C, 41.97; H, 3.19; N, 5.42.

Workup

  1. customwas fitted with a constant additional funnel
  2. customthe internal temperature between 0° C. and 2° C
  3. additionAfter the addition
  4. custom(~30 min)
  5. customthe light crystalline compound which precipitated
  6. filtrationwas filtered
  7. washwashed with 5% HBr
  8. washwashed several times with water (200 mL)
  9. customdried in a vacuum oven for 20 h at 40°-45° C.

Sources & evidence

ORD record
ord-792e1b4db5ac4da4a4730a5fe6f91281
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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