Ammonium Hydroxide → HCID 86632609, compound

HRID 2076122Notes

Reaction equation

HRID 2076122 reaction equation
[C:1]1([CH:7]2[C:12]3[N:13]=[C:14]([NH:16][C:17]4[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=4)[S:15][C:11]=3[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].[OH-].[NH4+:39]>CN(C)C=O>[CH3:26][O:27][C:24]1[CH:25]=[C:17]([NH:16][C:14]2[S:15][C:11]3[CH2:10][CH2:9][CH2:8][CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:12]=3[N:13]=2)[CH:18]=[CH:19][C:20]=1[C:21]([NH2:39])=[O:23]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 86632610HCID 86632610, compound

Product 1

HCID 86632609HCID 86632609, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzoic acid (810 mg, 2.1 mmol) and 1,1′-carbonyldiimidazol (463 mg, 2.8 mmol) in dimethylformamide (15 mL) was stirred for 30 minutes at 50° C. The solution was cooled to 0° C. and 25% aqueous ammonium hydroxide solution (1.6 mL, 21.3 mmol) was added slowly. The reaction mixture was stirred for 45 minutes at room temperature. The reaction was poured onto water, stirred for 15 minutes and the solid was filtered off, washed with water and dried to yield the title compound (661 mg, 82%) as an off-white solid. mp 243-246° C. MS ISP (m/e): 380.4 (100) [(M+H)+].

Workup

  1. additionThe reaction was poured onto water
  2. stirringstirred for 15 minutes
  3. filtrationthe solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a801589e2f9e45058259a077d379fe50
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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