Tert-Butylamine → HCID 920443, compound

HRID 2280402Notes

Reaction equation

HRID 2280402 reaction equation
[S-:1][C:2]#[N:3].[K+].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([NH:19][C:2]([NH:3][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][C:6]([Cl:5])=[CH:7][CH:8]=1)=[S:1])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 85014-Chlorobenzoyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 920443HCID 920443, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspension of potassium thiocyanate (KNCS) (611 mg, 6.29 mmol) in dichloromethane (30 mL) was added 200 μL of PEG-400 followed by 4-chlorobenzoyl chloride (1.00 g, 5.71 mmol). The suspension was heated to 40° C. for 2 h, then cooled to room temperature and filtered into an addition funnel. The solution was added dropwise into an ice cold solution of t-butylamine (418 mg, 5.71 mmol) in dichloromethane (30 mL). The reaction was stirred for 20 minutes following the complete addition, and then it was concentrated in vacuo delivering N-(tert-butylcarbamothioyl)-4-chlorobenzamide as a yellow solid (1.49 g, 96% yield). 1HNMR (400 MHz, DMSO-d6) δ 11.11 (s, 1H), 11.02 (s, 1H), 7.87 (d, 2H, J=8.8 Hz), 7.54 (d, 2H, J=8.4 Hz), 1.51 (s, 9H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered into an addition funnel
  3. additionthe complete addition
  4. concentrationit was concentrated in vacuo

Sources & evidence

ORD record
ord-e99d609f795048a2be5df3333624f264
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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