Allyl chloroformate → HCID 15549656, compound

HRID 381245Notes

Reaction equation

HRID 381245 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].Cl[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=[CH:8][C:9]=1[NH:10][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[O:4]

Participants

4

Reactant 2

HCID 18052Allyl chloroformateHCID 11994772Methyl 3-amino-5-(3-chlorophenyl)thiophene-2-carboxylate

Product 1

HCID 15549656HCID 15549656, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 3-Amino-5-(3-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester (15 g, 56.0 mmol) in toluene (200 mL) was added a solution of allyl chloroformate (8.10 g, 67.2 mmol) in toluene (5.0 mL) and the resulting reaction solution was heated under reflux for 3 h. Toluene was stripped down and the crystals were collected and washed with ether/hexane to afford a yellow crystalline compound, mp 101-103° C. 1H NMR (DMSO-d6) δ3.85 (s, 3H), 4.68-4.71 (d, 2H, J=5.46 Hz), 5.26-5.30 (dd, 1H, J=1.35, 9.84 Hz), 5.36-5.42 (dd, 1H, J=1.57, 15.68 Hz), 5.96(m, 2H), 7.50-7.52 (m, 2H), 7.67-7.71 (m, 1H), 7.79 (s, 1H), 8.10 (s, 1H); MS(+APCI) m/z 352(M+H); Anal. Calc. For C16H14ClNO4S: C, 54.63; H, 4.01; N, 3.97. Found: C, 54.05; H, 4.17; N, 3.84.

Workup

  1. customthe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux for 3 h
  4. customthe crystals were collected
  5. washwashed with ether/hexane
  6. customto afford a yellow crystalline compound, mp 101-103° C

Sources & evidence

ORD record
ord-a6b6d8937bfc47d1a2a1b3ee86c0090a
Source dataset
uspto-grants-2001_10
Patent number
US06306851B1

Reaction notes

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