2-Chloro-4-fluorobenzylamine → HCID 86704068, compound

HRID 2280403Notes

Reaction equation

HRID 2280403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].[S-:12][C:13]#[N:14].[K+].[Cl:16][C:17]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20]>C(#N)C.O>[Cl:16][C:17]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:18]=1[CH2:19][NH:20][C:13]([NH:14][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([F:1])[CH:3]=1)=[S:12]

Participants

6

Reactant 3

HCID 1399092-Chloro-4-fluorobenzylamineHCID 516872Potassium thiocyanateHCID 27245193,4-Difluorobenzoyl chloride

Product 1

HCID 86704068HCID 86704068, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3,4-diflorobenzoyl chloride (45 mL, 358 mmol) in acetonitrile (1.43 L) was added solid potassium thiocyanate (KNCS) (38.2 g, 393 mmol). The suspension was stirred to 0° C. for 10 min and then the cooling bath was removed. The suspension was stirred at room temperature for an additional 20 min. A solution of 2-chloro-4-fluorobenzylamine (57.1 g, 358 mmol) in acetonitrile (150 mL) was added over 5 minutes. The resulting suspension was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (1.4 L) and stirred for 1 hour. The suspension was filtered, rinsed with water (150 mL) and dried in vacuo at 60° C. to afford N-((2-chloro-4-fluorobenzyl)carbamothioyl)-3,4-difluorobenzamide as a yellow solid (98.3 g, 77% yield). 1HNMR (400 MHz, DMSO-d6) δ 11.56 (bs, 1H), 11.12 (t, 1H, J=5.7 Hz), 8.00 (m, 1H), 7.79 (m, 1H), 7.54 (m, 1H), 7.44 (m, 2H), 7.19 (m, 1H), 4.85 (d, 2H, J=5.7 Hz).

Workup

  1. customthe cooling bath was removed
  2. stirringThe suspension was stirred at room temperature for an additional 20 min
  3. stirringThe resulting suspension was stirred at room temperature for 3 hours
  4. stirringstirred for 1 hour
  5. filtrationThe suspension was filtered
  6. washrinsed with water (150 mL)
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-decc69064e8047298446919ef42e6b6a
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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